JP7244485B2 - Novel compound and organic electroluminescence device using the same - Google Patents

Description

TECHNICAL FIELD The present invention relates to novel compounds and organic electroluminescence devices using the same.

When a voltage is applied to an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device"), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

Patent Documents 1 and 2 disclose a compound in which an azine ring and a dibenzothiophene ring are bonded with or without a linking group, and an organic EL device using the compound, as a material for an organic EL device. .

WO2007/069569 WO2013/077352

An object of the present invention is to provide a novel compound capable of providing an organic electroluminescence device with high luminous efficiency, and an organic electroluminescence device using the compound with high luminous efficiency.

According to the present invention, the following novel compounds, electron-transporting materials for organic electroluminescence devices, organic electroluminescence and electronic devices are provided.
1. A compound represented by the following formula (1).

(In formula (1),
X ₁ is O or S;
Y ₁ , Y ₂ and Y ₃ are each independently CH or N;
provided that two or more of Y ₁ , Y ₂ and Y ₃ are N;
Ar ₁ and Ar ₃ are each independently
single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
It is a substituted or unsubstituted phenanthrylene group or a substituted or unsubstituted anthrylene group.
Ar ₂ and Ar ₄ are each independently
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted anthryl group,
is.
Ar ₁ and Ar ₂ , and Ar ₃ and Ar ₄ are each independently bonded to each other to form a ring consisting only of a substituted or unsubstituted saturated or unsaturated 6-membered ring, or form a ring do not form
However, the case where one or both of -Ar ₁ -Ar ₂ and -Ar ₃ -Ar ₄ is the following group is excluded.

2. An electron-transporting material for an organic electroluminescence device containing the compound represented by the above formula (1).
3. An organic electroluminescence device comprising an anode, an organic layer, and a cathode in this order,
The organic layer contains a compound represented by the above formula (1),
Organic electroluminescence device.
4. An organic electroluminescent device comprising an anode, a light-emitting layer, an electron-transporting zone, and a cathode in this order,
wherein the electron-transporting zone contains a compound represented by the above formula (1);
Organic electroluminescence device.
5. An electronic device comprising the above organic electroluminescence element.

ADVANTAGE OF THE INVENTION According to this invention, the novel compound which can provide the organic electroluminescent element with high luminous efficiency, and the organic electroluminescent element with high luminous efficiency using the same can be provided.

1 is a schematic diagram of an organic EL element according to one aspect of the present invention; FIG.

[definition]
In this specification, hydrogen atoms include isotopes with different numbers of neutrons, ie, protium, deuterium, and tritium, unless otherwise specified.

As used herein, the number of ring-forming carbon atoms refers to a compound having a structure in which atoms are cyclically bonded (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compounds, heterocyclic compounds). Represents the number of carbon atoms in an atom. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. Unless otherwise specified, the same applies to the "number of ring-forming carbon atoms" described below. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Further, for example, the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms, and the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
When the benzene ring or naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms in the alkyl group is not included in the number of ring-forming carbon atoms.

As used herein, the number of ring-forming atoms means a compound (e.g., monocyclic compound, condensed ring compound, bridged compound, carbocyclic compound, heterocyclic ring compound) represents the number of atoms constituting the ring itself. Atoms that do not constitute a ring (for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring) and atoms included in substituents when the ring is substituted by a substituent are not included in the number of ring-forming atoms. Unless otherwise specified, the same applies to the "number of ring-forming atoms" described below. For example, the pyridine ring has 6 ring-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming atoms. Hydrogen atoms bonded to carbon atoms of the pyridine ring and quinazoline ring and atoms constituting substituents are not included in the number of ring-forming atoms.

In the present specification, the expression “substituted or unsubstituted XX to YY carbon number ZZ group” means “carbon number XX to YY” represents the number of carbon atoms when the ZZ group is unsubstituted, and the substituted Do not include the number of carbon atoms in the substituents. Here, "YY" is greater than "XX", and "XX" and "YY" each mean an integer of 1 or more.

In the present specification, the term “substituted or unsubstituted ZZ group having an atomic number of XX to YY”, “the atomic number of XX to YY” represents the number of atoms when the ZZ group is unsubstituted, and the substituted Do not include the number of atoms of the substituents if they are present. Here, "YY" is greater than "XX", and "XX" and "YY" each mean an integer of 1 or more.

"Unsubstituted" when referring to a "substituted or unsubstituted ZZ group" means that the ZZ group is not substituted with a substituent and has a hydrogen atom attached. Alternatively, "substituted" when referring to a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced with a substituent. "Substituted" in the case of "a BB group substituted with an AA group" similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.

The substituents described in this specification are described below.
The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
The number of ring-forming atoms of the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified. be.
The number of carbon atoms in the "unsubstituted alkyl group" described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified. be.
The number of ring-forming carbon atoms of the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
The number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5, unless otherwise specified herein. ~18.
The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.

Specific examples of the "substituted or unsubstituted aryl group" described in this specification (specific example group G1) include the following unsubstituted aryl groups and substituted aryl groups. (Here, unsubstituted aryl group refers to the case where "substituted or unsubstituted aryl group" is "unsubstituted aryl group", and substituted aryl group is "substituted or unsubstituted aryl group" It refers to a "substituted aryl group".) Hereinafter, the term "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group".
A "substituted aryl group" is a case where an "unsubstituted aryl group" has a substituent, and the following "unsubstituted aryl group" includes a group having a substituent, a substituted aryl group, and the like. . The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are only examples, and the "substituted aryl group" described herein includes "unsubstituted aryl "Group" includes a group further having a substituent, such as a group having a substituent, and "substituted aryl group" further includes a group having a substituent.

Unsubstituted aryl group:
phenyl group,
a p-biphenyl group,
m-biphenyl group,
an o-biphenyl group,
p-terphenyl-4-yl group,
p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
anthryl group,
benzoanthryl group,
a phenanthryl group,
a benzophenanthryl group,
a phenalenyl group,
a pyrenyl group,
a chrysenyl group,
a benzochrysenyl group,
a triphenylenyl group,
a benzotriphenylenyl group,
a tetracenyl group,
pentacenyl group,
fluorenyl group,
9,9′-spirobifluorenyl group,
benzofluorenyl group,
a dibenzofluorenyl group,
a fluoranthenyl group,
a benzofluoranthenyl group,
Perylenyl group

Substituted aryl group:
an o-tolyl group,
m-tolyl group,
p-tolyl group,
para-xylyl group,
meta-xylyl group,
an ortho-xylyl group,
para-isopropylphenyl group,
meta-isopropylphenyl group,
an ortho-isopropylphenyl group,
para-t-butylphenyl group,
meta-t-butylphenyl group,
ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group 9,9-di(4-methylphenyl)fluorenyl group,
9,9-di(4-isopropylphenyl)fluorenyl group,
9,9-di(4-tbutylphenyl)fluorenyl group,
a cyanophenyl group,
a triphenylsilylphenyl group,
a trimethylsilylphenyl group,
a phenylnaphthyl group,
naphthylphenyl group

As used herein, a "heterocyclic group" is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
The "heterocyclic group" described herein may be a monocyclic group or a condensed ring group.
The "heterocyclic group" described herein may be either an aromatic heterocyclic group or an aliphatic heterocyclic group.
Specific examples of the "substituted or unsubstituted heterocyclic group" described herein (specific example group G2) include the following unsubstituted heterocyclic groups and substituted heterocyclic groups. (Here, unsubstituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”, and substituted heterocyclic group refers to “substituted or unsubstituted Heterocyclic group" refers to a "substituted heterocyclic group".) Hereinafter, when simply referred to as a "heterocyclic group", both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group" include.
"Substituted heterocyclic group" is a case where "unsubstituted heterocyclic group" has a substituent, and examples of the following "unsubstituted heterocyclic group" having a substituent and substituted heterocyclic groups etc. The examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described herein includes "unsubstituted A group in which a "substituted heterocyclic group" has a substituent, etc., and a group in which a "substituted heterocyclic group" further has a substituent are also included.

An unsubstituted heterocyclic group containing a nitrogen atom:
pyrrolyl group,
an imidazolyl group,
a pyrazolyl group,
a triazolyl group,
a tetrazolyl group,
an oxazolyl group,
an isoxazolyl group,
an oxadiazolyl group,
a thiazolyl group,
an isothiazolyl group,
a thiadiazolyl group,
a pyridyl group,
a pyridazinyl group,
a pyrimidinyl group,
pyrazinyl group,
a triazinyl group,
an indolyl group,
an isoindolyl group,
an indolizinyl group,
a quinolidinyl group,
quinolyl group,
an isoquinolyl group,
cinnolyl group,
a phthalazinyl group,
a quinazolinyl group,
a quinoxalinyl group,
a benzimidazolyl group,
an indazolyl group,
a phenanthrolinyl group,
a phenanthridinyl group,
acridinyl group,
phenazinyl group,
a carbazolyl group,
a benzocarbazolyl group,
a morpholino group,
a phenoxazinyl group,
a phenothiazinyl group,
azacarbazolyl group,
diazacarbazolyl group

An unsubstituted heterocyclic group containing an oxygen atom:
furyl group,
an oxazolyl group,
an isoxazolyl group,
an oxadiazolyl group,
xanthenyl group,
benzofuranyl group,
an isobenzofuranyl group,
a dibenzofuranyl group,
a naphthobenzofuranyl group,
a benzoxazolyl group,
a benzisoxazolyl group,
a phenoxazinyl group,
a morpholino group,
a dinaphthofuranyl group,
an azadibenzofuranyl group,
a diazadibenzofuranyl group,
azanaphthobenzofuranyl group,
diazanaphthobenzofuranyl group

An unsubstituted heterocyclic group containing a sulfur atom:
thienyl group,
a thiazolyl group,
an isothiazolyl group,
a thiadiazolyl group,
a benzothiophenyl group,
an isobenzothiophenyl group,
a dibenzothiophenyl group,
a naphthobenzothiophenyl group,
a benzothiazolyl group,
a benzoisothiazolyl group,
a phenothiazinyl group,
a dinaphthothiophenyl group,
an azadibenzothiophenyl group,
a diazadibenzothiophenyl group,
azanaphthobenzothiophenyl group,
diazanaphthobenzothiophenyl group

A substituted heterocyclic group containing a nitrogen atom:
(9-phenyl)carbazolyl group,
(9-biphenylyl)carbazolyl group,
(9-phenyl) phenylcarbazolyl group,
(9-naphthyl)carbazolyl group,
diphenylcarbazol-9-yl group,
a phenylcarbazol-9-yl group,
a methylbenzimidazolyl group,
ethylbenzimidazolyl group,
a phenyltriazinyl group,
a biphenylyltriazinyl group,
a diphenyltriazinyl group,
a phenylquinazolinyl group,
biphenylylquinazolinyl group

A substituted heterocyclic group containing an oxygen atom:
phenyldibenzofuranyl group,
methyldibenzofuranyl group,
a t-butyldibenzofuranyl group,
Monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene]

A substituted heterocyclic group containing a sulfur atom:
phenyldibenzothiophenyl group,
a methyldibenzothiophenyl group,
a t-butyldibenzothiophenyl group,
Monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene]

A monovalent group formed from the following unsubstituted heterocyclic ring containing at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and a monovalent group formed from the following unsubstituted heterocyclic ring are substituents: Groups having:

In formulas (XY-1) to (XY-18), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH, or CH ₂ . However, at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.
The heterocycles represented by the above formulas (XY-1) to (XY-18) have bonds at arbitrary positions to form monovalent heterocyclic groups.
The monovalent group formed from the unsubstituted heterocycles represented by the above formulas (XY-1) to (XY-18) has a substituent, which means that the A case where a hydrogen atom is replaced by a substituent, or X _A or Y _A is NH or CH ₂ and the hydrogen atom in these NH or CH ₂ is replaced by a substituent.

Specific examples of the "substituted or unsubstituted alkyl group" described in this specification (specific example group G3) include the following unsubstituted alkyl groups and substituted alkyl groups. (Here, unsubstituted alkyl group refers to the case where "substituted or unsubstituted alkyl group" is "unsubstituted alkyl group", and substituted alkyl group refers to the case where "substituted or unsubstituted alkyl group" is It refers to a "substituted alkyl group".) Hereinafter, simply referred to as an "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group".
A "substituted alkyl group" is a case where an "unsubstituted alkyl group" has a substituent, and the following "unsubstituted alkyl group" includes a group having a substituent and examples of a substituted alkyl group. . The examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification includes the "unsubstituted alkyl "Group" includes a group further having a substituent, such as a group having a substituent, and "substituted alkyl group" also includes a group further having a substituent.

unsubstituted alkyl group:
methyl group,
ethyl group,
n-propyl group,
isopropyl group,
n-butyl group,
isobutyl group,
s-butyl group,
t-butyl group

Substituted Alkyl Group:
a heptafluoropropyl group (including isomers),
pentafluoroethyl group,
2,2,2-trifluoroethyl group,
trifluoromethyl group

Specific examples of the "substituted or unsubstituted alkenyl group" described in the specification (specific example group G4) include the following unsubstituted alkenyl groups and substituted alkenyl groups. (Here, unsubstituted alkenyl group refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", "substituted alkenyl group" means "substituted or unsubstituted alkenyl group ” is a “substituted alkenyl group”.) Hereinafter, simply referred to as an “alkenyl group” includes both an “unsubstituted alkenyl group” and a “substituted alkenyl group”.
A "substituted alkenyl group" is a case where an "unsubstituted alkenyl group" has a substituent, and the following "unsubstituted alkenyl group" includes a group having a substituent, a substituted alkenyl group, and the like. . The examples of "unsubstituted alkenyl group" and "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described herein includes "unsubstituted alkenyl "Group" includes a group further having a substituent, and "substituted alkenyl group" includes a group further having a substituent.

Unsubstituted alkenyl group and substituted alkenyl group:
a vinyl group,
allyl group,
1-butenyl group,
2-butenyl group,
3-butenyl group,
1,3-butandienyl group,
1-methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-methylallyl group,
1,2-dimethylallyl group

Specific examples of the "substituted or unsubstituted alkynyl group" described in the specification (specific example group G5) include the following unsubstituted alkynyl groups. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) Hereinafter, simply referred to as "alkynyl group" means "unsubstituted includes both "alkynyl group" and "substituted alkynyl group".
A "substituted alkynyl group" is a case where an "unsubstituted alkynyl group" has a substituent, and examples thereof include groups in which the following "unsubstituted alkynyl group" has a substituent.

Unsubstituted alkynyl group:
ethynyl group

Specific examples of the "substituted or unsubstituted cycloalkyl group" described in the specification (specific example group G6) include the following unsubstituted cycloalkyl groups and substituted cycloalkyl groups. (Here, unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group", and substituted cycloalkyl group refers to "substituted or unsubstituted Refers to the case where "cycloalkyl group" is "substituted cycloalkyl group".) Hereinafter, when simply referred to as "cycloalkyl group", both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" include.
A "substituted cycloalkyl group" is a case where an "unsubstituted cycloalkyl group" has a substituent, and examples of the following "unsubstituted cycloalkyl group" having a substituent or a substituted cycloalkyl group etc. The examples of "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" listed here are only examples, and the "substituted cycloalkyl group" described herein includes "unsubstituted A group in which a "substituted cycloalkyl group" has a substituent, etc., and a group in which a "substituted cycloalkyl group" further has a substituent are also included.

Unsubstituted Aliphatic Ring Group:
a cyclopropyl group,
cyclobutyl group,
a cyclopentyl group,
a cyclohexyl group,
1-adamantyl group,
2-adamantyl group,
1-norbornyl group,
2-norbornyl group

Substituted cycloalkyl group:
4-methylcyclohexyl group

Specific examples of the group represented by —Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) described in the specification (specific example group G7) include:
-Si (G1) (G1) (G1)
- Si (G1) (G2) (G2)
-Si (G1) (G1) (G2)
- Si (G2) (G2) (G2)
- Si (G5) (G5) (G5)
- Si (G6) (G6) (G6)
is mentioned.
here,
G1 is an "aryl group" as described in specific example group G1.
G2 is a "heterocyclic group" as described in Specific Example Group G2.
G3 is an "alkyl group" as described in specific example group G3.
G6 is a "cycloalkyl group" as described in Specific Example Group G6.

Specific examples of the group represented by —O—(R ₉₀₄ ) described in the specification (specific example group G8) include:
-O (G1)
-O (G2)
-O (G3)
-O (G6)
is mentioned.
here,
G1 is an "aryl group" as described in specific example group G1.
G2 is a "heterocyclic group" as described in Specific Example Group G2.
G3 is an "alkyl group" as described in specific example group G3.
G6 is a "cycloalkyl group" as described in Specific Example Group G6.

Specific examples of the group represented by -S-(R ₉₀₅ ) described in the specification (specific example group G9) include:
-S (G1)
-S (G2)
-S (G3)
-S (G6)
is mentioned.
here,
G1 is an "aryl group" as described in specific example group G1.
G2 is a "heterocyclic group" as described in Specific Example Group G2.
G3 is an "alkyl group" as described in specific example group G3.
G6 is a "cycloalkyl group" as described in Specific Example Group G6.

Specific examples of the group represented by —N(R ₉₀₆ )(R ₉₀₇ ) described in the specification (specific example group G10) include:
-N (G1) (G1)
-N (G2) (G2)
-N (G1) (G2)
-N (G3) (G3)
-N (G6) (G6)
is mentioned.
here,
G1 is an "aryl group" as described in specific example group G1.
G2 is a "heterocyclic group" as described in Specific Example Group G2.
G3 is an "alkyl group" as described in specific example group G3.
G6 is a "cycloalkyl group" as described in Specific Example Group G6.

Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.

A specific example of the “alkoxy group” described in this specification is a group represented by —O(G3), where G3 is the “alkyl group” described in Specific Example Group G3. The carbon number of the "unsubstituted alkoxy group" is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
A specific example of the "alkylthio group" described in this specification is a group represented by -S(G3), where G3 is the "alkyl group" described in Specific Example Group G3. The carbon number of the "unsubstituted alkylthio group" is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
A specific example of the “aryloxy group” described herein is a group represented by —O(G1), where G1 is the “aryl group” described in Specific Example Group G1. The number of ring-forming carbon atoms in the "unsubstituted aryloxy group" is 6-50, preferably 6-30, more preferably 6-18, unless otherwise specified in the specification.
A specific example of the “arylthio group” described herein is a group represented by —S(G1), where G1 is the “aryl group” described in Specific Example Group G1. The number of ring-forming carbon atoms in the "unsubstituted arylthio group" is 6-50, preferably 6-30, more preferably 6-18, unless otherwise specified in the specification.
A specific example of the "aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is an "alkyl group" described in Specific Example Group G3. , G1 are "aryl groups" as described in specific example group G1. Therefore, an "aralkyl group" is one aspect of a "substituted alkyl group" substituted with an "aryl group". The number of carbon atoms in the "unsubstituted aralkyl group" which is the "unsubstituted alkyl group" substituted by the "unsubstituted aryl group" is 7 to 50, preferably 7, unless otherwise specified in the specification. ~30, more preferably 7-18.
Specific examples of the "aralkyl group" include, for example, benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2- β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group and the like.

A substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl- 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, 9,9-diphenylfluorenyl group and the like.

The substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenyl, unless otherwise stated herein. nantholinyl group, carbazolyl group, benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothio phenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenyl Carbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, phenyldibenzothiophenyl group and the like.

The above dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in the present specification.

In formulas (XY-76) to (XY-79), X _B is an oxygen atom or a sulfur atom.

The substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, unless otherwise stated herein. base etc.

Unless otherwise specified, the “substituted or unsubstituted arylene group” described herein refers to a divalent version of the above “aryl group”. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups of the "aryl group" described in the specific example group G1.

Specific examples of the "substituted or unsubstituted divalent heterocyclic group" described in this specification (specific example group G13) include a divalent group of the "heterocyclic group" described in specific example group G2, and the like. is mentioned.

Specific examples of the "substituted or unsubstituted alkylene group" described in this specification (specific example group G14) include divalent "alkyl group" described in specific example group G3.

A substituted or unsubstituted arylene group described herein is preferably any one of the following groups, unless otherwise specified in the specification.

In formulas (XY-20) to (XY-29), R ₉₀₈ is a substituent.
m901 is an integer of 0 to 4, and when m901 is 2 or more, a plurality of R ₉₀₈ may be the same or different.

In formulas (XY-30) to (XY-40), each R ₉₀₉ is independently a hydrogen atom or a substituent. Two R ₉₀₉ may be joined together through a single bond to form a ring.

In formulas (XY-41) to (XY-46), R ₉₁₀ is a substituent.
m902 is an integer from 0 to 6. When m902 is 2 or more, multiple _R910 may be the same or different.

Unless otherwise stated, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any one of the following groups.

In formulas (XY-50) to (XY-64), R ₉₁₁ is a hydrogen atom or a substituent.

In the above formulas (XY-65) to (XY-75), X _B is an oxygen atom or a sulfur atom.

As used herein, the following formula ( An anthracene compound represented by XY-80) will be described as an example.

For example, when "one or more pairs of two or more adjacent R ₉₂₁ to R ₉₃₀ are bonded to each other to form a ring", two adjacent pairs forming one pair are R ₉₂₁ and R ₉₂₂ , _R922 and _R923 , _R923 and _R924 , _{R924 and} R930, R930 and _R925 , _R925 and _R926 , _R926 and _R927 , _R927 and _R928 , _R928 and _R929 , _and R ₉₂₉ and _R921 .

The above-mentioned "one or more pairs" means that two or more pairs of the adjacent two groups may form a ring at the same time. For example, when R ₉₂₁ and R ₉₂₂ are bonded together to form ring A, and R ₉₂₅ and R ₉₂₆ are bonded together to form ring B, the following formula (XY-81) .

When "two or more adjacent" form a ring, for example, R ₉₂₁ and R ₉₂₂ are bonded together to form ring A, and R ₉₂₂ and R ₉₂₃ are bonded together to form ring C. When three of R ₉₂₁ to R ₉₂₃ adjacent to each other form ring A and ring C sharing R ₉₂₂ fused to the anthracene backbone, the ring is represented by the following formula (XY-82).

Rings A to C formed in the above formulas (XY-81) and (XY-82) are saturated or unsaturated rings.
"Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. A "saturated ring" means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.
For example, in the above formula (XY-81), ring A formed by bonding R ₉₂₁ and R ₉₂₂ together is the carbon atom of the anthracene skeleton to which R ₉₂₁ is bound and the carbon atom of the anthracene skeleton to which R ₉₂₂ is bound. It means a ring formed by an atom and one or more arbitrary elements. As a specific example, when R ₉₂₁ and R ₉₂₂ form Ring A, the carbon atom of the anthracene skeleton to which R ₉₂₁ is bound, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bound, and four carbon atoms are dissociated. When forming a saturated ring, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring. Moreover, when forming a saturated ring, it becomes a cyclohexane ring.

Here, the "arbitrary elements" are preferably C elements, N elements, O elements, and S elements. In any element (for example, in the case of C element or N element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with any substituent. When any element other than the C element is included, the formed ring is a heterocyclic ring.
"One or more arbitrary elements" constituting a saturated or unsaturated ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, still more preferably 3 or more and 5 or less. .

When the above "saturated or unsaturated ring" has a substituent, the substituent is as described above.

In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (hereinafter sometimes referred to as "optional substituent") is
an unsubstituted alkyl group having 1 to 50 carbon atoms,
an unsubstituted alkenyl group having 2 to 50 carbon atoms,
an unsubstituted alkynyl group having 2 to 50 carbon atoms,
an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ )
(here,
R ₉₀₁ to R ₉₀₇ are each independently
hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more R ₉₀₁ to R ₉₀₇ are present, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different. ),
halogen atom, cyano group, nitro group,
It is a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituents referred to above as "substituted or unsubstituted" are
an alkyl group having 1 to 50 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituents referred to above as "substituted or unsubstituted" are
an alkyl group having 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.

Specific examples of each group of the optional substituents are as described above.

In the present specification, unless otherwise specified, any adjacent substituents are saturated or unsaturated rings (preferably substituted or unsubstituted saturated or unsaturated, 5- or 6-membered rings, or Preferably, a benzene ring) may be formed.
In this specification, any substituent may further have a substituent unless otherwise specified. Substituents further possessed by the optional substituents include those similar to the above optional substituents.

[Compound represented by formula (1)]
A novel compound of one embodiment of the present invention is represented by the following formula (1).

(In formula (1),
X ₁ is O or S;
Y ₁ , Y ₂ and Y ₃ are each independently CH or N;
provided that two or more of Y ₁ , Y ₂ and Y ₃ are N;
Ar ₁ and Ar ₃ are each independently
single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
It is a substituted or unsubstituted phenanthrylene group or a substituted or unsubstituted anthrylene group.
Ar ₂ and Ar ₄ are each independently
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted anthryl group,
is.
Ar ₁ and Ar ₂ , and Ar ₃ and Ar ₄ are each independently bonded to each other to form a ring consisting only of a substituted or unsubstituted saturated or unsaturated 6-membered ring, or form a ring do not form
However, the case where one or both of -Ar ₁ -Ar ₂ and -Ar ₃ -Ar ₄ is the following group is excluded.

The compound represented by the above formula (1) has excellent solubility in a solvent and is easy to synthesize and purify, so that a highly pure compound can be obtained. Compounds with low solubility make it difficult to sufficiently increase the purity of materials, and organic EL devices using materials with low purity tend to deteriorate and their efficiency tends to decrease. On the other hand, if the compound represented by the formula (1), which is highly soluble, is used as a material for an organic EL device, the efficiency is high and good device performance is likely to be exhibited.

Here, "a ring consisting only of a 6-membered ring" means a ring in which the number of ring-forming atoms in one ring is 6, and 3- to 5-membered rings and 7-membered rings or more are excluded. means that The saturated 6-membered ring is cyclohexane, and the unsaturated 6-membered ring includes a benzene ring and the like. Specifically, for example, groups derived from a fluorene ring containing a five-membered ring in addition to a benzene ring are excluded.
The “ring consisting only of a 6-membered ring” includes a 6-membered monocyclic ring and a ring in which two or more 6-membered rings are condensed.
In addition, arbitrary substituents may substitute the ring which consists only of 6-membered rings.

In one embodiment,
Ar ₂ and Ar ₄ are each independently
an unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
It is a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted anthryl group.

In one embodiment,
When Ar ₁ and Ar ₃ are unsubstituted phenylene groups, Ar ₂ and Ar ₄ are each independently
an unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
It is a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted anthryl group.

In one embodiment,
one of Ar ₁ and Ar ₃ is a single bond,
the other is a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
It is a substituted or unsubstituted phenanthrylene group or a substituted or unsubstituted anthrylene group.

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (2). That is, _X1 is S.

(In formula (2), Y ₁ to Y ₃ and Ar ₁ to Ar ₄ are as defined in formula (1) above.)

In one embodiment, the compound represented by the formula (1) is one or more selected from compounds represented by the following formula (3A) and compounds represented by the following formula (3B), and A compound represented by (3A) is preferred. That is, Y ₁ to Y ₃ are N.

(In formulas (3A) and (3B), X ₁ and Ar ₁ to Ar ₄ are as defined in formula (1) above.)
Y ₁ to Y ₃ are N in the formula (3A), and Y ₁ is CH, and Y ₂ and Y ₃ are N in the formula (3B).

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (4).

(In Formula (4), Ar ₁ to Ar ₄ are as defined in Formula (1) above.)
The formula (4) is such that X ₁ is S in the formula (3A).

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (5).

(In formula (5), Ar ₂ to Ar ₄ are as defined in formula (1) above.)

In one embodiment, Ar ₁ and Ar ₂ and Ar ₃ and Ar ₄ are each independently not joined together to form a ring.

In one embodiment, when Ar ₁ -Ar ₄ are substituted, the substituents are
an unsubstituted phenyl group,
an unsubstituted naphthyl group,
an unsubstituted phenanthryl group,
an unsubstituted anthryl group,
an unsubstituted biphenyl group,
It is an unsubstituted alkyl group having 1 to 50 carbon atoms or an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

In one embodiment, -Ar ₁ -Ar ₂ and -Ar ₃ -Ar ₄ are each independently selected from the group consisting of groups represented by formulas (a1) to (a11) below.

(In the formulas (a1) to (a11),
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each m is independently an integer of 0 to 5.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
Each q is independently an integer of 0 to 2.
r is an integer of 0 or 1;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. )
(R _a )r in the above formula (a10) represents R _a when r is 1, and represents a hydrogen atom when r is 0.

In one embodiment, -Ar ₁ -Ar ₂ and -Ar ₃ -Ar ₄ are each independently selected from the group consisting of groups represented by formulas (aa1) to (aa8) below.

(In the formulas (aa1) to (aa8),
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each m is independently an integer of 0 to 5.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
q is an integer from 0 to 2;
r is an integer of 0 or 1;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. )
(R _a )r in the above formula (aa7) represents R _a when r is 1, and represents a hydrogen atom when r is 0.

In one embodiment, -Ar ₁ -Ar ₂ and -Ar ₃ -Ar ₄ are each independently selected from the group consisting of groups represented by formulas (ab1) to (ab7) below.

(In the formulas (ab1) to (ab7),
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each m is independently an integer of 0 to 5.
Each n is independently an integer of 0-4.
p is an integer from 0 to 3;
q is an integer from 0 to 2;
r is an integer of 0 or 1;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. )
(R _a )r in the above formula (ab6) represents R _a when r is 1, and represents a hydrogen atom when r is 0.

In one embodiment, -Ar ₁ -Ar ₂ and -Ar ₃ -Ar ₄ are each independently selected from the group consisting of groups represented by formulas (ac1) to (ac93) below.

(In formulas (ac1) to (ac93),
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
A substituted or unsubstituted anthryl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each m is independently an integer of 0 to 5.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
Each q is independently an integer of 0 to 2.
Each r is independently an integer of 0 or 1.
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. )
(R _a )r in the above formula (ab6) represents R _a when r is 1, and represents a hydrogen atom when r is 0.

R _a in the formulas (a1) to (a11), (aa1) to (aa8), (ab1) to (ab7) and ( _ac1 ) to ( _ac93 ) is a substituent when substituted or a substituent when the substituent is further substituted with an arbitrary substituent, and in one embodiment, R _a is unsubstituted alkyl having 1 to 50 carbon atoms or an unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.

In one embodiment, two or more adjacent pairs of R _a are not joined together to form a ring.

In one embodiment, m, n, p, q and r are zero. This means that Ar ₁ to Ar ₄ in the above formula (1) are not substituted with a substituent.

In one embodiment, Ar ₂ and Ar ₄ are each independently
an unsubstituted phenyl group,
an unsubstituted naphthyl group,
It is an unsubstituted anthryl group or an unsubstituted phenanthryl group.

In one embodiment, Ar ₁ and Ar ₃ are each independently
single bond,
It is an unsubstituted p-phenylene group or an unsubstituted 1,4-naphthylene group.

In the above formulas (1), (2), (3A), (3B), (4), (5), (a1) to (a11), (aa1) to (aa8) and (ab1) to (ab7) The details of each substituent and the substituent in the case of "substituted or unsubstituted" are as described in the [Definition] column of the present specification.

In one embodiment, the following compounds are excluded from the compounds represented by formula (1).

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (6).

(In formula (6), X ₁ , Y ₁ to Y ₃ , Ar ₁ , Ar ₂ and Ar ₄ are as defined in formula (1) above.
Ar _3A is a phenylene group, naphthylene group, phenanthrylene group, or anthrylene group comprising a benzene ring substituted with Ar ₄ at least at the ortho position, and has one or more substituents other than Ar ₄ ; may be )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (6-1).

[In Formula (6-1), X ₁ , Y ₁ to Y ₃ , Ar ₂ and Ar ₄ are as defined in Formula (1) above.
Ar _3A is as defined in formula (6) above.
Ar _1a is a divalent group selected from the following group.

(Wherein, _Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
q is an integer from 0 to 2;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. )]

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (6-2).

(In Formula (6-2), X ₁ , Y ₁ to Y ₃ , Ar ₂ and Ar ₄ are as defined in Formula (1) above.
Ar _3A is as defined in formula (6) above.
Ar _1A is a phenylene group, naphthylene group, phenanthrylene group, or anthrylene group comprising a benzene ring substituted with Ar ₂ at least at the ortho position, and has one or more substituents other than Ar ₂ ; may be )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (7).

(In Formula (7), X ₁ , Y ₁ and Ar ₁ to Ar ₄ are as defined in Formula (1) above.
The compound according to claim 1, provided that at least one of Ar ₁ to Ar ₄ is a monovalent or divalent group containing a substituted or unsubstituted naphthalene ring or phenanthrene ring.

In one embodiment, at least one of Ar ₁ to Ar ₄ in formula (7) is the following monovalent or divalent group consisting of a substituted or unsubstituted naphthalene ring.

(In the formula, *1 is a bond with a nitrogen-containing heterocycle or Ar ₁ or Ar ₃ .
*2 is a bond with _Ar2 or _Ar4 .
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
q is an integer from 0 to 2;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are 2 or more R _a , two or more adjacent R _a pairs do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (7-1).

(In formula (7-1), X ₁ , Y ₁ , Ar ₂ , Ar ₃ and Ar ₄ are as defined in formula (1) above.
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
n is an integer from 0 to 4;
p is an integer from 0 to 3;
However, n+p is 6 or less.
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are 2 or more R _a , two or more adjacent R _a pairs do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (7-2).

(In formula (7-2), X ₁ , Y ₁ to Y ₃ , Ar ₂ , Ar ₃ and Ar ₄ are as defined in formula (1) above.
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
n is an integer from 0 to 4;
p is an integer from 0 to 3;
However, n+p is 6 or less.
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are 2 or more R _a , two or more adjacent R _a pairs do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. )

In one embodiment, the compound represented by the formula (7) is a compound represented by the following formula (7-3).

(In Formula (7-3), X ₁ , Y ₁ , Ar ₂ to Ar ₄ are as defined in Formula (1) above.
Ar _1B is a divalent group selected from the following group.

(Wherein, _Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
n is an integer from 0 to 4;
Each p is independently an integer of 0-3.
r is an integer of 0 or 1;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are 2 or more R _a , two or more adjacent R _a pairs do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (7-4).

(In formula (7-4), X ₁ , Y ₁ , Ar ₂ and Ar ₄ are as defined in formula (1) above.
Ar _1C is a divalent group selected from the following group.

(Wherein, _Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
n is an integer from 0 to 4;
Each p is independently an integer of 0-3.
r is an integer of 0 or 1;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are 2 or more R _a , two or more adjacent R _a pairs do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.
Ar _3A is a phenylene group, naphthylene group, phenanthrylene group, or anthrylene group comprising a benzene ring substituted with Ar ₄ at least at the ortho position, and has one or more substituents other than Ar ₄ ; may be )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (8).

(In Formula (8), X ₁ , Y ₁ , Ar ₂ and Ar ₄ are as defined in Formula (1) above.
Ar _1D and Ar _3D are each independently a divalent group selected from the following group.

(Wherein, _Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
q is an integer from 0 to 2;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are 2 or more R _a , two or more adjacent R _a pairs do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (9).

(In Formula (9), X ₁ , Y ₁ , Ar ₃ and Ar ₄ are as defined in Formula (1) above.
Ar _1E is a phenylene group, a naphthylene group, a phenanthrylene group, or an anthrylene group comprising at least a benzene ring substituted with a phenyl group at the meta position, and one or more groups other than the phenyl group substituted at the meta position; may have a substituent of
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
n is an integer from 0 to 4;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. )

In one embodiment, the compound represented by the formula (9) is a compound represented by the following formula (9-1).

(In formula (9-1), X ₁ , Y ₁ and Ar ₄ are as defined in formula (1) above.
Ar _1E , R _a and n are as defined in formula (9) above.
q is an integer from 0 to 2; )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (9-2).

(In formula (9-2), X ₁ , Y ₁ , Ar ₁ and Ar ₄ are as defined in formula (1) above.
Ar _1E , R _a and n are as defined in formula (9) above.
Ar _3B is
a substituted or unsubstituted naphthylene group,
It is a substituted or unsubstituted phenanthrylene group or a substituted or unsubstituted anthrylene group. )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (10).

(In Formula (10), X ₁ , Y ₁ and Ar ₄ are as defined in Formula (1) above.
Ar _1E is a phenylene group, naphthylene group, phenanthrylene group, or anthrylene group comprising a benzene ring substituted with Ar _2A at least at the meta position, and has one or more substituents other than Ar _2A ; may be
Ar _2A is
a substituted or unsubstituted naphthyl group,
It is a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted anthryl group.
Ar _3B is
a substituted or unsubstituted naphthylene group,
It is a substituted or unsubstituted phenanthrylene group or a substituted or unsubstituted anthrylene group. )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (10-1).

(In formula (9-1), X ₁ , Y ₁ and Ar ₄ are as defined in formula (1) above.
Ar _1E is a phenylene group, naphthylene group, phenanthrylene group, or anthrylene group comprising a benzene ring substituted with Ar _2A at least at the meta position, and has one or more substituents other than Ar _2A ; may be
Ar _2A is
a substituted or unsubstituted naphthyl group,
It is a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted anthryl group.
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
q is an integer from 0 to 2;
When there are two Ra _'s , the two Ra _'s may be the same or different. )

Specific examples of the compound represented by formula (1) are described below, but these are only examples, and the compound represented by formula (1) is not limited to the following specific examples.

The compound represented by the above formula (1) can be produced by following the method described in the examples below and using known alternative reactions and raw materials that are suitable for the desired product.

[Electron transport material for organic EL device]
The compound represented by Formula (1) of one embodiment of the present invention is useful as a material for an organic EL device, and is particularly useful as an electron-transporting material or a phosphorescent host.
An electron-transporting material for an organic electroluminescence device according to one aspect of the present invention contains the compound represented by the formula (1).

[Organic electroluminescence device]
An organic electroluminescence element of one embodiment of the present invention comprises
An organic electroluminescence device comprising an anode, an organic layer, and a cathode in this order,
The organic layer contains the compound represented by the above formula (1).
The compound represented by the above formula (1) may be contained in any of the layers when there are a plurality of organic layers. The type of organic layer will be described later.

Further, the organic electroluminescence element of one embodiment of the present invention includes
An organic electroluminescent device comprising an anode, a light-emitting layer, an electron-transporting zone, and a cathode in this order,
The electron transport zone contains the compound represented by formula (1) above.

In one embodiment, the electron-transporting zone comprises the first electron-transporting layer and the second electron-transporting layer in the order of the light-emitting layer, the first electron-transporting layer, the second electron-transporting layer and the cathode;
At least one of the first electron-transporting layer and the second electron-transporting layer contains the compound represented by formula (1) above.
By containing the compound represented by the formula (1) in either or both of the first electron-transporting layer and the second electron-transporting layer, an organic EL device with high luminous efficiency can be obtained.

A schematic configuration of an organic EL element according to one aspect of the present invention will be described with reference to FIG.
An organic EL element 1 according to one aspect of the present invention has a substrate 2, an anode 3, an organic thin film layer 4, a light emitting layer 5, an organic thin film layer 6 and a cathode 10 in this order. The organic thin film layer 4 located between the anode 3 and the light emitting layer 5 functions as a hole transport zone and the organic thin film layer 6 located between the light emitting layer 5 and the cathode 10 functions as an electron transport zone. .
The organic thin film layer 6 includes a first electron transport layer 6a located on the light emitting layer 5 side and a second electron transport layer 6b located on the cathode 10 side.
Either or both of the first electron transport layer 6a and the second electron transport layer 6b contain the compound represented by the formula (1). By including the compound represented by the formula (1) in the first electron transport layer 6a or the second electron transport layer 6b, an organic EL device with improved luminous efficiency can be obtained.

In one embodiment, the light-emitting layer contains a compound represented by the following formula (11).

(In formula (11),
R ₁₁ to R ₁₈ are each independently
hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are each independently
hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more R ₉₀₁ to R ₉₀₇ are present, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different.
Two or more adjacent ones of R ₁₁ to R ₁₄ and two or more adjacent ones of R ₁₅ to R ₁₈ do not combine to form a ring.
L ₁₁ and L ₁₂ are each independently
single bond,
It is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
Ar ₁₁ and Ar ₁₂ are each independently
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. )

By including the compound represented by the formula (11) in the light-emitting layer, an organic EL device with further improved light-emitting efficiency can be obtained.

In one embodiment, the compound represented by the formula (11) is a compound represented by the following formula (12).

[In Formula (12), R ₁₁ to R ₁₈ , L ₁₁ and L ₁₂ are as defined in Formula (11) above.
At least one of Ar _11a and Ar _12a is a monovalent group represented by the following formula (20).

(In formula (20),
one of R ₂₁ to R ₂₈ is a bond that binds to L ₁₁ or L ₁₂ ;
R ₂₁ to R ₂₈ that are not bonds that bind to L ₁₁ or L ₁₂ are
each independently a hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in formula (11) above.
Adjacent two or more of R ₂₁ to R ₂₈ which are not bonds to L ₁₁ or L ₁₂ do not bond to each other to form a ring. )
Ar _11a or Ar _12a , which is not a monovalent group represented by the formula (20),
A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms other than the monovalent group represented by the formula (20) It is a cyclic group. ]

In one embodiment, the compound represented by the formula (12) is a compound represented by the following formula (12-1).

(In Formula (12-1), R ₁₁ to R ₁₈ , L ₁₁ and L ₁₂ are as defined in Formula (11) above.
Ar _12a is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted 5 to 50 ring-forming atoms other than the monovalent group represented by the formula (20) It is a monovalent heterocyclic group.
R ₂₁ and R ₂₃ to R ₂₈ are each independently a hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in formula (11) above. )

In one embodiment, the compound represented by the formula (11) is a compound represented by the following formula (13).

(In Formula (13), R ₁₁ to R ₁₈ , L ₁ and L ₂ are as defined in Formula (11) above.
Ar _11b and Ar _12b are each independently
It is a substituted or unsubstituted aryl group composed only of a benzene ring having 6 to 50 ring-forming carbon atoms. )

In one embodiment, the compound represented by the formula (13) is a compound represented by the following formula (13-1).

(In formula (13-1), R ₁₁ to R ₁₈ and L ₁₂ are as defined in formula (11) above.
Ar _11b and Ar _12b are each independently a substituted or unsubstituted aryl group consisting of a benzene ring having 6 to 50 ring-forming carbon atoms. )

Here, an aryl group "consisting only of a benzene ring" means that an aryl group containing a ring other than a benzene ring is excluded. Specifically, groups derived from a fluorene ring containing a five-membered ring in addition to a benzene ring are excluded.
An aryl group "consisting only of a benzene ring" includes a group consisting of a single benzene ring (i.e., phenyl group), a group in which two or more benzene rings are continuously bonded via a single bond (e.g., a biphenylyl group etc.), and groups consisting of condensed benzene rings (eg, naphthyl group, etc.).
An aryl group consisting of only a benzene ring may be substituted with any substituent.

In one embodiment, Ar _11b and Ar _12b are each independently
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted biphenylyl group,
A substituted or unsubstituted terphenylyl group, a substituted or unsubstituted anthryl group, or a substituted or unsubstituted phenanthryl group.

In one embodiment, the compound represented by the formula (11) is a compound represented by the following formula (14).

式（３０）中、
Ｒ_３１～Ｒ_３４のうちの隣接する２つ又はＲ_３５～Ｒ_３８のうちの隣接する２つは、互いに結合して下記式（４０）で表される不飽和の環を形成する。

式（４０）中、
＊は、Ｒ_３１～Ｒ_３４のうちの隣接する２つ又はＲ_３５～Ｒ_３８のうちの隣接する２つとの結合位置である。
前記式（４０）で表される不飽和の環を形成しないＲ_３１～Ｒ_３８、及びＲ_４１～Ｒ_４４のうちの隣接する２つ以上は、互いに結合して環を形成しない。
前記式（４０）で表される不飽和の環を形成しないＲ_３１～Ｒ_３８及びＲ_４１～Ｒ_４４のうちの１つはＬ_１１又はＬ_１２と結合する結合手であり、
前記式（４０）で表される不飽和の環を形成せず、かつＬ_１１又はＬ_１２と結合する結合手ではないＲ_３１～Ｒ_３８、及びＬ_１１又はＬ_１２と結合する結合手ではないＲ_４１～Ｒ_４４は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ_９０１）（Ｒ_９０２）（Ｒ_９０３）、
－Ｏ－（Ｒ_９０４）、
－Ｓ－（Ｒ_９０５）、
－Ｎ（Ｒ_９０６）（Ｒ_９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｒ_９０１～Ｒ_９０７は、前記式（１１）で定義した通りである。］[In Formula (14), R ₁₁ to R ₁₈ , L ₁₁ and L ₁₂ are as defined in Formula (11) above.
At least one of Ar _11c and Ar _12c is a monovalent group represented by the following formula (30).

In formula (30),
Adjacent two of R ₃₁ to R ₃₄ or adjacent two of R ₃₅ to R ₃₈ are bonded to each other to form an unsaturated ring represented by the following formula (40).

In formula (40),
* is a bonding position with adjacent two of R ₃₁ to R ₃₄ or adjacent two of R ₃₅ to R ₃₈ .
Adjacent two or more of R ₃₁ to R ₃₈ and R ₄₁ to R ₄₄ that do not form an unsaturated ring represented by formula (40) do not combine to form a ring.
one of R ₃₁ to R ₃₈ and R ₄₁ to R ₄₄ that does not form an unsaturated ring represented by the formula (40) is a bond that bonds to L ₁₁ or L ₁₂ ;
R ₃₁ to R ₃₈ that do not form an unsaturated ring represented by the formula (40) and are not a bond that bonds to L ₁₁ or L ₁₂ , and are not a bond that bonds to L ₁₁ or L ₁₂ R ₄₁ to R ₄₄ are each independently
hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in formula (11) above. ]

In one embodiment, the monovalent group represented by formula (30) is selected from monovalent groups represented by formulas (30A) to (30F) below.

(In formulas (30A) to (30C), R ₃₁ to R ₃₈ and R ₄₁ to R ₄₄ are as defined in formula (14) above.)

In one embodiment, the compound represented by the formula (11) is a compound represented by the following formula (15).

[In Formula (15), R ₁₁ to R ₁₈ , L ₁₁ and L ₁₂ are as defined in Formula (11) above.
At least one of Ar _11d and Ar _12d is a monovalent group represented by the following formula (50).
Ar _11d and Ar _12d , which are not monovalent groups represented by the following formula (50),
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When both Ar _11d and Ar _12d are monovalent groups represented by the following formula (50), the monovalent groups Ar _11d and Ar _12d represented by the following formula (50) are identical to each other. There may be, or they may be different.

(In formula (50),
R ₅₁ and R ₅₂ are each independently
hydrogen atom, halogen atom, cyano group, nitro group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
It is a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
R ₅₁ and R ₅₂ are not combined with each other to form a ring.
Two or more adjacent pairs of R ₅₃ to R ₆₀ are bonded to each other to form an unsaturated ring represented by the following formula (60), or an unsaturated ring represented by the following formula (60) Does not form saturated rings.

In formula (60), *** is a bonding position with two adjacent ones of R ₅₃ to R ₆₀ .
When two or more adjacent pairs of R ₅₃ to R ₆₀ are bonded to each other to form an unsaturated ring represented by the formula (60), the unsaturated ring represented by the formula (60) One of R ₅₃ to R ₆₀ and R ₆₁ to R ₆₄ that do not form a ring of is a single bond that bonds to L ₁₁ or L ₁₂ .
When two or more unsaturated rings represented by formula (60) are formed, the plurality of R ₆₁ to R ₆₄ may be the same or different.
When two or more adjacent pairs of R ₅₃ to R ₆₀ do not combine with each other to form an unsaturated ring represented by the formula (60), one of R ₅₃ to R ₆₀ is It is a single bond that binds to _L11 or _L12 .
In the case of forming the unsaturated ring represented by the formula (60) and in the case of not forming the unsaturated ring represented by the formula (60), the unsaturated ring represented by the formula (60) Two or more adjacent pairs of R ₅₃ to R ₆₀ that do not form a ring and are not single bonds bonded to L ₁₁ or L ₁₂ are bonded to each other and are represented by the formula (60) Forms a substituted or unsubstituted saturated or unsaturated ring other than an unsaturated ring, or does not form a substituted or unsubstituted saturated or unsaturated ring.
does not form an unsaturated ring represented by the formula (60), does not form a substituted or unsubstituted saturated or unsaturated ring other than the unsaturated ring represented by the formula (60), and R ₅₃ to R ₆₀ that are not single bonds _bonded to L ₁₁ or L ₁₂ and R ₆₁ to R ₆₄ that are not single bonds bonded to L ₁₁ or L 12 are each independently
hydrogen atom, halogen atom, cyano group, nitro group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in formula (11) above. ]

In one embodiment, the compound represented by the formula (15) is a compound represented by the following formula (15-1).

(In formula (15-1), R ₁₁ to R ₁₈ , L ₁₁ , L ₁₂ and R ₅₁ to R ₆₀ are as defined in formula (15) above.
Ar _12e is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted 5 to 50 ring-forming atoms, other than the monovalent group represented by the formula (50) It is a monovalent heterocyclic group. )

In one embodiment, R ₁₁ to R ₁₈ in formulas (11) to (15) are hydrogen atoms.
In one embodiment, L ₁₁ and L ₁₂ in formulas (11) to (15) are each independently
single bond,
an unsubstituted phenylene group,
An unsubstituted naphthylene group, an unsubstituted biphenyldiyl group, or an unsubstituted terphenyldiyl group.

In one embodiment, one or both of the first electron-transporting layer and the second electron-transporting layer further comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, Alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and rare earth metals contains one or more selected from the group consisting of organic complexes containing

In one embodiment, there is a hole-transporting layer between the anode and the light-emitting layer.

Hereinafter, the layer structure of the organic EL element according to one aspect of the present invention will be described.
An organic EL device according to one aspect of the present invention includes an organic layer between a pair of electrodes consisting of a cathode and an anode. The organic layer includes at least one layer containing an organic compound. Alternatively, the organic layer is formed by laminating a plurality of layers containing an organic compound. The organic layer may have a layer consisting only of one or more organic compounds. The organic layer may have a layer containing both an organic compound and an inorganic compound. The organic layer may have a layer consisting only of one or more inorganic compounds.
At least one of the layers included in the organic layers is a light-emitting layer. The organic layer may be configured as, for example, a single light-emitting layer, or may include other layers that may be employed in the layer configuration of the organic EL device. Layers that can be employed in the layer structure of the organic EL device are not particularly limited. electron-blocking layer, exciton-blocking layer, etc.), light-emitting layer, space layer, electron-transporting zone provided between the cathode and the light-emitting layer (electron-transporting layer, electron-injecting layer, hole-blocking layer, etc.).

The organic EL device according to one aspect of the present invention may be, for example, a fluorescent or phosphorescent monochromatic light emitting device, or a fluorescent/phosphorescent hybrid white light emitting device. Moreover, it may be a simple type having a single light emitting unit, or a tandem type having a plurality of light emitting units.
The term “light-emitting unit” refers to a minimum unit that includes organic layers, at least one of which is a light-emitting layer, and emits light through recombination of injected holes and electrons.
Also, the “light-emitting layer” described in this specification is an organic layer having a light-emitting function. The light-emitting layer is, for example, a phosphorescent light-emitting layer, a fluorescent light-emitting layer, or the like, and may be one layer or multiple layers.
The light-emitting unit may be a laminated type having a plurality of phosphorescent-emitting layers and fluorescent-emitting layers. In this case, for example, a space layer is provided to prevent excitons generated in the phosphorescent-emitting layer from diffusing into the fluorescent-emitting layer. between each light-emitting layer.

Simple type organic EL elements include, for example, an element configuration such as anode/light-emitting unit/cathode.
A representative layer structure of the light-emitting unit is shown below. Layers in brackets are optional.
(a) (hole injection layer/) hole transport layer/fluorescent layer (/electron transport layer/electron injection layer)
(b) (Hole Injection Layer/) Hole Transport Layer/Phosphorescent Emitting Layer (/Electron Transport Layer/Electron Injection Layer)
(c) (Hole Injection Layer/) Hole Transport Layer/First Fluorescent Layer/Second Fluorescent Layer (/Electron Transport Layer/Electron Injection Layer)
(d) (hole injection layer/) hole transport layer/first phosphorescent-emitting layer/second phosphorescent-emitting layer (/electron transport layer/electron injection layer)
(e) (Hole injection layer/) Hole transport layer/Phosphorescent layer/Space layer/Fluorescent layer (/Electron transport layer/Electron injection layer)
(f) (Hole Injection Layer/) Hole Transport Layer/First Phosphorescent-Emitting Layer/Second Phosphorescent-Emitting Layer/Space Layer/Fluorescent Emitting Layer (/Electron Transport Layer/Electron Injection Layer)
(g) (Hole Injection Layer/) Hole Transport Layer/First Phosphorescent Layer/Space Layer/Second Phosphorescent Layer/Space Layer/Fluorescent Layer (/Electron Transport Layer/Electron Injection Layer)
(h) (Hole Injection Layer/) Hole Transport Layer/Phosphorescent Layer/Space Layer/First Fluorescent Layer/Second Fluorescent Layer (/Electron Transport Layer/Electron Injection Layer)
(i) (Hole Injection Layer/) Hole Transport Layer/Electron Blocking Layer/Fluorescent Emitting Layer (/Electron Transport Layer/Electron Injection Layer)
(j) (Hole Injection Layer/) Hole Transport Layer/Electron Blocking Layer/Phosphorescent Emitting Layer (/Electron Transport Layer/Electron Injection Layer)
(k) (Hole Injection Layer/) Hole Transport Layer/Exciton Blocking Layer/Fluorescence Emitting Layer (/Electron Transport Layer/Electron Injection Layer)
(l) (Hole Injection Layer/) Hole Transport Layer/Exciton Blocking Layer/Phosphorescent Emitting Layer (/Electron Transport Layer/Electron Injection Layer)
(m) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescent layer (/electron transport layer/electron injection layer)
(n) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescence emitting layer (/first electron transport layer/second electron transport layer/electron injection layer)
(o) (Hole injection layer/) First hole transport layer/Second hole transport layer/Phosphorescent layer (/Electron transport layer/Electron injection layer)
(p) (hole-injection layer/) first hole-transport layer/second hole-transport layer/phosphorescence-emitting layer (/first electron-transport layer/second electron-transport layer/electron-injection layer)
(q) (hole-injection layer/) hole-transport layer/fluorescence-emitting layer/hole-blocking layer (/electron-transport layer/electron-injection layer)
(r) (Hole Injection Layer/) Hole Transport Layer/Phosphorescent Layer/Hole Blocking Layer (/Electron Transport Layer/Electron Injection Layer)
(s) (hole injection layer/) hole transport layer/fluorescence emitting layer/exciton blocking layer (/electron transport layer/electron injection layer)
(t) (Hole Injection Layer/) Hole Transport Layer/Phosphorescent Emitting Layer/Exciton Blocking Layer (/Electron Transport Layer/Electron Injection Layer)

However, the layer structure of the organic EL element according to one aspect of the present invention is not limited to these. For example, when the organic EL device has a hole injection layer and a hole transport layer, it is preferable that the hole injection layer is provided between the hole transport layer and the anode. Moreover, when the organic EL device has an electron injection layer and an electron transport layer, it is preferable that the electron injection layer is provided between the electron transport layer and the cathode. Moreover, each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of one layer or may be composed of a plurality of layers.

The plurality of phosphorescent-emitting layers, and the phosphorescent-emitting layer and the fluorescent-emitting layer may be light-emitting layers of different colors. For example, the light-emitting unit (f) includes a hole-transporting layer/first phosphorescent-emitting layer (red-emitting)/second phosphorescent-emitting layer (green-emitting)/space layer/fluorescent-emitting layer (blue-emitting)/electron-transporting layer. You can also
An electron-blocking layer may be provided between each light-emitting layer and the hole-transporting layer or space layer. A hole-blocking layer may be provided between each light-emitting layer and the electron-transporting layer. By providing an electron-blocking layer or a hole-blocking layer, electrons or holes can be confined in the light-emitting layer, the recombination probability of charges in the light-emitting layer can be increased, and the luminous efficiency can be improved.

A typical element configuration of the tandem-type organic EL element includes, for example, an element configuration such as anode/first light-emitting unit/intermediate layer/second light-emitting unit/cathode.
The first lighting unit and the second lighting unit can, for example, be independently selected from the lighting units described above.
Intermediate layers are also commonly referred to as intermediate electrodes, intermediate conductive layers, charge generating layers, electron withdrawal layers, connecting layers, connector layers, or intermediate insulating layers. The intermediate layer is a layer that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit, and can be made of a known material.

The function, material, etc. of each layer of the organic EL element described in this specification will be described below.

(substrate)
The substrate is used as a support for organic EL elements. The substrate preferably has a transmittance of 50% or more for light in the visible light region with a wavelength of 400 to 700 nm, and is preferably smooth. Examples of substrate materials include soda lime glass, aluminosilicate glass, quartz glass, and plastics. Alternatively, a flexible substrate can be used as the substrate. A flexible substrate refers to a (flexible) substrate that can be bent, and includes, for example, a plastic substrate. Specific examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic deposition films can also be used.

(anode)
As the anode, it is preferable to use, for example, a metal, an alloy, a conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more). Specific examples of materials for the anode include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and oxide containing zinc oxide. Examples include indium and graphene. Also included are gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, and nitrides of these metals (eg, titanium nitride).

An anode is usually formed by depositing these materials on a substrate by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method using a target in which 1 to 10% by mass of zinc oxide is added to indium oxide. In addition, for example, indium oxide containing tungsten oxide or zinc oxide is obtained by using a target in which 0.5 to 5% by mass of tungsten oxide or 0.1 to 1% by mass of zinc oxide is added to indium oxide. , can be formed by a sputtering method.
Other methods for forming the anode include, for example, a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method, and the like. For example, when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

The hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode. Therefore, common electrode materials such as metals, alloys, conductive compounds, and mixtures thereof can be used for the anode. Specifically, alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (eg, magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium a material with a low work function, such as an alloy containing rare earth metals, can also be used for the anode.

(hole injection layer)
The hole injection layer is a layer containing a substance having a high hole injection property and has a function of injecting holes from the anode into the organic layer. Examples of highly hole-injecting substances include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. compounds, tungsten oxides, manganese oxides, aromatic amine compounds, electron-withdrawing (acceptor) compounds, polymer compounds (oligomers, dendrimers, polymers, etc.). Among these, aromatic amine compounds and acceptor compounds are preferred, and acceptor compounds are more preferred.

Specific examples of aromatic amine compounds include 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3 -methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4, 4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[ N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation : PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)- N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and the like.

Preferred examples of the acceptor compound include heterocyclic derivatives having an electron-withdrawing group, quinone derivatives having an electron-withdrawing group, arylborane derivatives, and heteroarylborane derivatives. 3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (abbreviation: F4TCNQ), 1,2,3-tris[(cyano)(4-cyano-2,3,5, 6-tetrafluorophenyl)methylene]cyclopropane and the like.
When an acceptor compound is used, the hole injection layer preferably further contains a matrix material. As the matrix material, a material known as a material for organic EL devices can be used, and for example, an electron-donating (donor) compound is preferably used.

(Hole transport layer)
The hole-transporting layer is a layer containing a highly hole-transporting substance and has a function of transporting holes from the anode to the organic layer.

Substances with high hole-transport properties are preferably substances having a hole mobility of 10 ⁻⁶ cm ² /(V·s) or more. Examples include molecular compounds.

Specific examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)- N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: TPD) : BAFLP), 4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4′,4″-tris(N, N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4 '-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and the like.

Specific examples of carbazole derivatives include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), 9 -Phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA) and the like.

Specific examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth) and the like.

Specific examples of the polymer compound include poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA).

Substances other than these may be used in the hole-transporting layer as long as the compounds have higher hole-transporting properties than electron-transporting properties.

The hole transport layer may be a single layer, or may be a laminate of two or more layers. In this case, a layer containing a substance with a large energy gap among substances with high hole-transport properties is preferably arranged on the side closer to the light-emitting layer.

(Light emitting layer)
The light-emitting layer is a layer containing a highly luminescent substance (dopant material). Various materials can be used as the dopant material, and for example, a fluorescent compound (fluorescent dopant), a phosphorescent compound (phosphorescent dopant), and the like can be used. A fluorescent light-emitting compound is a compound capable of emitting light from a singlet excited state, and a light-emitting layer containing this is called a fluorescent light-emitting layer. A phosphorescent compound is a compound capable of emitting light from a triplet excited state, and a light-emitting layer containing this is called a phosphorescent light-emitting layer.

The light-emitting layer usually contains a dopant material and a host material for efficient light emission. Note that the dopant material may also be referred to as a guest material, an emitter, or a light-emitting material in some documents. Also, the host material may be referred to as a matrix material in some documents.
A single light-emitting layer may contain multiple dopant materials and multiple host materials. Also, a plurality of light-emitting layers may be provided.

A host material combined with a fluorescent dopant is referred to herein as a "fluorescent host", and a host material combined with a phosphorescent dopant is referred to herein as a "phosphorescent host". Note that the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. A phosphorescent host is a material for forming a phosphorescent layer containing a phosphorescent dopant, but this does not mean that it cannot be used as a material for forming a fluorescent layer. The same is true for fluorescent hosts.

The content of the dopant material in the light emitting layer is not particularly limited, but from the viewpoint of sufficient light emission and concentration quenching, it is preferably, for example, 0.1 to 70% by mass, more preferably 0.1% by mass. 1 to 30% by mass, more preferably 1 to 30% by mass, even more preferably 1 to 20% by mass, and particularly preferably 1 to 10% by mass.

<Fluorescent dopant>
Examples of fluorescent dopants include condensed polycyclic aromatic derivatives, styrylamine derivatives, condensed ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives and the like. Among these, condensed ring amine derivatives, boron-containing compounds, and carbazole derivatives are preferred.
Examples of condensed ring amine derivatives include diaminopyrene derivatives, diaminochrysene derivatives, diaminoanthracene derivatives, diaminofluorene derivatives, and diaminofluorene derivatives in which one or more benzofuro skeletons are fused.
Boron-containing compounds include, for example, pyrromethene derivatives, triphenylborane derivatives and the like.

Examples of blue fluorescent dopants include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Specifically, N,N′-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4-(9H -carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H -carbazol-3-yl)triphenylamine (abbreviation: PCBAPA) and the like.

Green fluorescent dopants include, for example, aromatic amine derivatives. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1 '-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N ',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N' , N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1′-biphenyl-2-yl)]-N-[4-(9H-carbazole -9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.

Examples of red fluorescent dopants include tetracene derivatives and diamine derivatives. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N', and N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).

<Phosphorescent dopant>
Examples of phosphorescent dopants include phosphorescent heavy metal complexes and phosphorescent rare earth metal complexes.
Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes. The heavy metal complexes are preferably ortho-metallated complexes of metals selected from iridium, osmium and platinum.
Examples of rare earth metal complexes include terbium complexes and europium complexes. Specifically, tris (acetylacetonate) (monophenanthroline) terbium (III) (abbreviation: Tb(acac) ₃ (Phen)), tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) phenanthroline) europium (III) (abbreviation: Eu(DBM) ₃ (Phen)), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline) europium (III) (abbreviation: Eu(DBM) 3 (Phen)) : Eu(TTA) ₃ (Phen)) and the like. These rare earth metal complexes are preferred as phosphorescent dopants because electron transitions between different multiplicities cause the rare earth metal ions to emit light.

Examples of blue phosphorescent dopants include iridium complexes, osmium complexes, and platinum complexes. Specifically, bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4′ ,6′-difluorophenyl)pyridinato-N,C2′]iridium (III) picolinate (abbreviation: FIrpic), bis[2-(3′,5′-bistrifluoromethylphenyl)pyridinato-N,C2′]iridium ( III) picolinate (abbreviation: Ir(CF3ppy) ₂ (pic)), bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III) acetylacetonate (abbreviation: FIracac), etc. is mentioned.

Examples of greenish phosphorescent dopants include iridium complexes. Specifically, tris(2-phenylpyridinato-N,C2′)iridium(III) (abbreviation: Ir(ppy) ₃ ), bis(2-phenylpyridinato-N,C2′)iridium(III) ) acetylacetonate (abbreviation: Ir(ppy) ₂ (acac)), bis(1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir(pbi) ₂ (acac)) , bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq) ₂ (acac)), and the like.

Examples of red phosphorescent dopants include iridium complexes, platinum complexes, terbium complexes, europium complexes, and the like. Specifically, bis[2-(2′-benzo[4,5-α]thienyl)pyridinato-N,C3′]iridium(III) acetylacetonate (abbreviation: Ir(btp) ₂ (acac)), bis(1-phenylisoquinolinato-N,C2′)iridium(III) acetylacetonate (abbreviation: Ir(piq) ₂ (acac)), (acetylacetonato)bis[2,3-bis(4-fluoro Phenyl)quinoxalinato]iridium (III) (abbreviation: Ir(Fdpq) ₂ (acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum (II) (abbreviation: : PtOEP) and the like.

<Host material>
Examples of host materials include metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; Heterocyclic compounds such as azole derivatives, benzimidazole derivatives, and phenanthroline derivatives; condensed aromatic compounds such as naphthalene derivatives, triphenylene derivatives, carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, naphthacene derivatives, and fluoranthene derivatives; Examples include aromatic amine compounds such as amine derivatives and condensed polycyclic aromatic amine derivatives. A plurality of host materials may be used in combination.

Specific examples of metal complexes include tris(8-quinolinolato)aluminum (III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (III) (abbreviation: Almq3), bis(10-hydroxybenzo [h]quinolinato)beryllium (II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-quinolinolato)zinc ( II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc (II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc (II) (abbreviation: ZnBTZ) and the like.

Specific examples of heterocyclic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5 -(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4- tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and the like.

Specific examples of the condensed aromatic compound include 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10- Phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene ( Abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9′-bianthryl (abbreviation: BANT), 9,9′-(stilbene- 3,3′-diyl)diphenanthrene (abbreviation: DPNS), 9,9′-(stilbene-4,4′-diyl)diphenanthrene (abbreviation: DPNS2), 3,3′,3″-(benzene-1 ,3,5-triyl)tripylene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene and the like.

Specific examples of aromatic amine compounds include N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10 -Phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA) ), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10- diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4, 4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi, 4,4'-bis[N-(spiro-9,9'-bifluorene- 2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and the like.

The fluorescent host is preferably a compound having a singlet level higher than that of the fluorescent dopant, and examples thereof include heterocyclic compounds and condensed aromatic compounds. Preferred examples of condensed aromatic compounds include anthracene derivatives, pyrene derivatives, chrysene derivatives, naphthacene derivatives, and the like.

The phosphorescent host is preferably a compound having a triplet level higher than that of the phosphorescent dopant, and examples thereof include metal complexes, heterocyclic compounds, condensed aromatic compounds, and the like. Compounds represented by the formula (1) are also included. Among these, for example, indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc. preferable.

(Electron transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. Substances with high electron-transport properties are preferably substances having an electron mobility of 10 ⁻⁶ cm ² /Vs or more. Examples include metal complexes, aromatic heterocyclic compounds, aromatic hydrocarbon compounds, and polymer compounds. etc.

Examples of metal complexes include aluminum complexes, beryllium complexes, and zinc complexes. Specifically, tris(8-quinolinolato)aluminum (III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) (abbreviation: Znq), bis [2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and the like.

Examples of aromatic heterocyclic compounds include imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives and benzimidazophenanthridine derivatives; azine derivatives such as pyrimidine derivatives and triazine derivatives; quinoline derivatives, isoquinoline derivatives and phenanthroline derivatives. Examples thereof include compounds containing a nitrogen six-membered ring structure (including those having a phosphine oxide-based substituent on the heterocyclic ring). Specifically, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert- butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)- 1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: : p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), and the like.

Examples of aromatic hydrocarbon compounds include anthracene derivatives and fluoranthene derivatives.

Specific examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9 ,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like.

Substances other than these may be used in the electron-transporting layer as long as the compounds have higher electron-transporting properties than hole-transporting properties.

The electron transport layer may be a single layer, or may be a laminate of two or more layers. In this case, it is preferable to dispose a layer containing a substance having a large energy gap among substances having a high electron-transport property, on the side closer to the light-emitting layer.

The electron transport layer includes, for example, alkali metals, magnesium, alkaline earth metals, metals such as alloys containing two or more of these metals; alkali metal compounds such as 8-quinolinolatritium (abbreviation: Liq); Metal compounds such as alkaline earth metal compounds may also be included. When metals such as alkali metals, magnesium, alkaline earth metals, or alloys containing two or more of these metals are contained in the electron-transporting layer, the content thereof is not particularly limited. .1 to 50% by mass, more preferably 0.1 to 20% by mass, still more preferably 1 to 10% by mass.
When a metal compound such as an alkali metal compound or an alkaline earth metal compound is contained in the electron transport layer, the content is preferably 1 to 99% by mass, more preferably 10 to 90% by mass. is. When the electron transport layer has a plurality of layers, the layer on the light emitting layer side can also be formed only from these metal compounds.

(Electron injection layer)
The electron injection layer is a layer containing a substance with high electron injection properties and has a function of efficiently injecting electrons from the cathode to the light emitting layer. Substances with high electron injection properties include, for example, alkali metals, magnesium, alkaline earth metals, and compounds thereof. Specific examples include lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, and lithium oxide. Alternatively, a substance having an electron-transporting property containing an alkali metal, magnesium, an alkaline earth metal, or a compound thereof, such as Alq containing magnesium, can be used.

A composite material containing an organic compound and a donor compound can also be used for the electron injection layer. Since the organic compound receives electrons from the donor compound, such composite materials are excellent in electron injection and electron transport properties.
As the organic compound, a substance that is excellent in transporting received electrons is preferable. For example, the metal complex, the aromatic heterocyclic compound, or the like, which is a substance with high electron transporting property, can be used.
The donor compound may be any substance that can donate electrons to an organic compound, and examples thereof include alkali metals, magnesium, alkaline earth metals, and rare earth metals. Specific examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like. Further, alkali metal oxides and alkaline earth metal oxides are preferred, and specific examples include lithium oxide, calcium oxide, barium oxide and the like. Lewis bases such as magnesium oxide can also be used. An organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

(cathode)
The cathode is a metal, an alloy, a conductive compound, a mixture thereof, or the like, and preferably has a small work function (specifically, 3.8 eV or less). Materials for the cathode include, for example, alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (eg, magnesium-silver, aluminum-lithium); rare earth metals; alloys containing rare earth metals;
A cathode is usually formed by a vacuum deposition method or a sputtering method. Moreover, when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

In addition, when an electron injection layer is provided, regardless of the magnitude of the work function, various conductive materials such as aluminum, silver, ITO, graphene, silicon or indium oxide-tin oxide containing silicon oxide are used to form the cathode. can be formed. These conductive materials can be deposited using a sputtering method, an inkjet method, a spin coating method, or the like.

(insulating layer)
Since an organic EL element applies an electric field to a thin film, pixel defects due to leaks and short circuits are likely to occur. To prevent this, a thin insulating layer may be inserted between the pair of electrodes.
Specific examples of substances used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, oxide Silicon, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like. A mixture of these substances can be used for the insulating layer, and a laminate of a plurality of layers containing these substances can also be used.

(space layer)
For example, when a fluorescent-emitting layer and a phosphorescent-emitting layer are laminated, the space layer is provided between both layers to prevent diffusion of excitons generated in the phosphorescent-emitting layer into the fluorescent-emitting layer and to adjust carrier balance. be provided. A space layer can also be provided, for example, between a plurality of phosphorescent-emitting layers.
Since the space layer is provided between a plurality of light-emitting layers, it is preferably formed using a material having both electron-transport properties and hole-transport properties. Moreover, from the viewpoint of preventing diffusion of triplet energy in adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or more.
Materials used for the space layer include the same materials as those used for the hole transport layer.

(Electron blocking layer, hole blocking layer, exciton blocking layer)
An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, or the like may be provided adjacent to the light-emitting layer.
The electron-blocking layer is a layer having a function of blocking electrons from leaking from the light-emitting layer to the hole-transporting layer. A hole-blocking layer is a layer having a function of blocking leakage of holes from a light-emitting layer to an electron-transporting layer. The exciton-blocking layer is a layer that has the function of blocking excitons generated in the light-emitting layer from diffusing to adjacent layers and confining the excitons within the light-emitting layer.

(capping layer)
An organic EL device can have a capping layer on top of the cathode in order to adjust the intensity of extracted light by the optical interference effect.
Examples of capping layers that can be used include polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitrides, and silicon compounds (silicon oxide, etc.).
Aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives can also be used in the capping layer.
A laminate obtained by stacking layers containing these substances can also be used as the capping layer.

(middle layer)
An intermediate layer is provided in the tandem-type organic EL device.

(Layer forming method)
The method for forming each layer of the organic EL element is not particularly limited unless otherwise specified. As a forming method, a known method such as a dry film forming method or a wet film forming method can be used. Specific examples of the dry film forming method include a vacuum vapor deposition method, a sputtering method, a plasma method, an ion plating method and the like. Specific examples of the wet film forming method include various coating methods such as spin coating, dipping, flow coating, and inkjet.

(film thickness)
The thickness of each layer of the organic EL element is not particularly limited unless otherwise specified. If the film thickness is too small, defects such as pinholes are likely to occur, and sufficient luminance cannot be obtained. On the other hand, if the film thickness is too large, a high driving voltage is required and the efficiency is lowered. From this point of view, the film thickness is usually preferably 1 nm to 10 μm, more preferably 1 nm to 0.2 μm.

[Electronics]
An electronic device according to one aspect of the present invention includes the above-described organic EL element according to one aspect of the present invention. Specific examples of electronic devices include display components such as organic EL panel modules; display devices such as televisions, mobile phones, smart phones, and personal computers; and light-emitting devices such as lighting and vehicle lamps.

EXAMPLES Next, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to the description of these Examples.

Synthesis Example 1 (synthesis of compound ET-1)

2,4-bis(4-biphenyl-yl)-6-chloro-1,3,5-triazine (5.0 g) and dibenzothiophene-4-boronic acid (3.0 g) in dimethoxyethane (200 mL) In addition, argon gas was bubbled through the solution for 5 minutes. Tetrakis(triphenylphosphine)palladium (0.55 g) and an aqueous sodium carbonate solution (2M, 18 mL) were added thereto, and the mixture was stirred under reflux with heating for 5 hours under an argon atmosphere. After cooling to room temperature, the precipitated solid was collected by filtration and washed with methanol and water. 200 mL of chlorobenzene was added to this solid and dissolved by heating, and the insoluble matter was removed by filtration through celite. The solid precipitated by concentration under reduced pressure was recrystallized with toluene to obtain compound ET-1 (5.8 g, yield 86%). The molecular weight of compound ET-1 was 567.71, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 567, so it was identified as compound ET-1. .

Synthesis Example 2 (synthesis of compound ET-2)
(1) Synthesis of intermediate A

2-(4-biphenylyl)-4,6-dichloro-1,3,5-triazine (2.0 g) and 2-biphenylboronic acid (1.18 g) were dissolved in dimethoxyethane (90 mL) and added to the solution. Argon gas was passed through for 5 minutes. To this was added tetrakis(triphenylphosphine)palladium (15 mg) and aqueous potassium carbonate (2M, 10 mL) and heated to 65° C. for 5 hours with stirring under an argon atmosphere. The reaction solution was subjected to column chromatography to obtain Intermediate A (0.8 g, yield 29%).

(2) Synthesis of compound ET-2

Intermediate A (0.8 g) and dibenzothiophene-4-boronic acid (0.65 g) were added to dimethoxyethane (30 mL) and argon gas was bubbled through the solution for 5 minutes. To this was added tetrakis(triphenylphosphine)palladium (4.0 mg) and aqueous potassium carbonate solution (2M, 3.0 mL) and heated to 65° C. for 3 hours with stirring under an argon atmosphere. The reaction solution was subjected to column chromatography to obtain compound ET-2 (0.70 g, yield 65%). The molecular weight of compound ET-2 was 567.71, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 567, so it was identified as compound ET-2. .

Synthesis Example 3 (synthesis of compound ET-3)
(1) Synthesis of intermediate B

2,4-Dichloro-6-phenyl-1,3,5-triazine (5.0 g), dibenzothiophene-4-boronic acid (4.5 g) and tetrakis(triphenylphosphine)palladium (0.5 g) were mixed with dimethoxyethane ( 221 mL), and the inside of the container was replaced with nitrogen. After that, a 2M sodium carbonate aqueous solution (33 mL) was added, and the mixture was heated to 80° C. under a nitrogen atmosphere and stirred for 6 hours. Water was added to the reaction solution, and the precipitated solid was collected by filtration. The solid was washed with acetone to give Intermediate B (5.0 g, 60% yield).

(2) Synthesis of Intermediate C

9-([1,1′-biphenyl]-2-yl)-10-bromoanthracene (10.0 g) and 4-chlorophenylboronic acid (3.8 g) were dissolved in dimethoxyethane (244 mL), and tetrakis ( Triphenylphosphine)palladium (0.35 g) was added and the inside of the vessel was replaced with nitrogen. After that, 2M aqueous sodium carbonate solution (37 mL) was added, and the mixture was heated to 75° C. under a nitrogen atmosphere and stirred overnight. The reaction solution was purified by column chromatography to obtain Intermediate C (10.1 g, yield 94%).

(3) Synthesis of Intermediate D

Intermediate C (12.6 g), bis(pinacolato)diboron (7.3 g), potassium acetate (8.4 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1. 1 g) and tris(dibenzylideneacetone) dipalladium (1.0 g) were added to 1,4-dioxane (286 mL), and the inside of the vessel was replaced with nitrogen. After that, the mixture was heated to 100° C. under a nitrogen atmosphere and stirred for 6 hours. The reaction solution was purified by column chromatography to obtain Intermediate D (14.0 g, yield 91%).

(4) Synthesis of compound ET-3

Intermediate B (4.6 g), Intermediate D (5.2 g), and tetrakis(triphenylphosphine)palladium (0.4 g) were added to dimethoxyethane (123 mL), and the inside of the vessel was purged with nitrogen. After that, 2M sodium carbonate aqueous solution (18 mL) was added, heated to reflux under nitrogen atmosphere, and stirred overnight. Methanol was added to the reaction solution, and the precipitated solid was collected by filtration. The solid was recrystallized with toluene to obtain compound ET-3 (7.7 g, yield 84%). The molecular weight of compound ET-3 was 743.93, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 743, so it was identified as compound ET-3. .

Synthesis Example 4 (synthesis of compound ET-4)
(1) Synthesis of Intermediate E

Cyanuric chloride (5.0 g) and 2-biphenylboronic acid (21 g) were dissolved in toluene (271 mL), dichlorobis(triphenylphosphine)palladium (0.04 g) was added, and the reaction vessel was purged with argon. After that, 2M potassium carbonate aqueous solution (81 mL) was added, heated to 50° C. under an argon atmosphere, and stirred for 12 hours. The reaction solution was purified by column chromatography to obtain Intermediate E (5.0 g, 22% yield).

(2) Synthesis of compound ET-4

Intermediate E (5.0 g) and dibenzothiophene-4-boronic acid (3.3 g) were dissolved in dimethoxyethane (120 mL), tetrakis(triphenylphosphine)palladium (0.55 g) was added, and the inside of the vessel was flushed with argon. replaced. After that, a 2M sodium carbonate aqueous solution (18 mL) was added, and the mixture was heated under reflux for 5 hours under an argon atmosphere. The reaction solution was concentrated, and the obtained solid was recrystallized with toluene to obtain compound ET-4 (4.8 g, yield 71%). The molecular weight of compound ET-4 was 567.71, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 567, so it was identified as compound ET-4. .

Synthesis Example 5 (synthesis of compound ET-5)
(1) Synthesis of intermediate F

2-(4-biphenylyl)-4,6-dichloro-1,3,5-triazine (0.5 g) and [1,1′:3′,1″-terphenyl]-3-yl-boronic acid (Synthesized according to the description of Japanese Patent No. 5357150B2) (0.5 g) and dichlorobis(triphenylphosphine)palladium (1.1 mg) were dissolved in toluene (8 mL), and the inside of the vessel was replaced with argon. After that, a 2M sodium carbonate aqueous solution (33 mL) was added, and the mixture was heated to 60° C. under an argon atmosphere and stirred for 4 hours. Water was added to the reaction solution, and the precipitated solid was collected by filtration. The solid was recrystallized with toluene to give Intermediate F (0.46 g, 57% yield).

(2) Synthesis of compound ET-5

Intermediate F (0.47 g) and dibenzothiophene-4-boronic acid (0.32 g) were dissolved in dimethoxyethane (9.4 mL), tetrakis(triphenylphosphine) palladium (43 mg) was added, and the inside of the vessel was filled with argon. replaced. After that, a 2M sodium carbonate aqueous solution (1.2 mL) was added, and the mixture was heated under reflux for 3 hours under an argon atmosphere. The reaction solution was concentrated, and the obtained solid was recrystallized with toluene to obtain compound ET-5 (0.4 g, yield 66%). The molecular weight of compound ET-5 was 643.81, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 643, so it was identified as compound ET-5. .

Synthesis Example 6 (synthesis of compound ET-6)
(1) Synthesis of intermediate G

4-bromodibenzothiophene (5.0 g) was dissolved in tetrahydrofuran (50 mL). The reaction vessel was cooled to −78° C. under an argon atmosphere, and 1.6 M n-butyllithium solution (14 mL) was added dropwise to this solution. After stirring for 30 minutes, this solution was added dropwise over 30 minutes to a solution of cyanuric chloride (3.5 g) in tetrahydrofuran (50 mL) cooled to -78°C. After stirring overnight at room temperature, the solvent was distilled off under reduced pressure, and the precipitated solid was washed with acetone to obtain Intermediate G (2.6 g, yield 41%).

(2) Synthesis of compound ET-6

Intermediate G (2.5 g) and 4-(9-phenanthrenyl)phenyl-boronic acid (synthesized as described in US Pat. No. 8,940,412 B2) (1.4 g) were dissolved in dimethoxyethane (40 mL) and tetrakis(triphenylphosphine) Palladium (0.1 g) was added. After purging the inside of the container with argon, 2M potassium carbonate aqueous solution (13 mL) was added, and the mixture was stirred while heating under reflux for 4 hours. Water was added to the reaction solution, and the precipitated solid was collected by filtration. After washing the solid with dichloromethane, it was recrystallized with toluene to obtain compound ET-6 (0.9 g, 28%). The molecular weight of compound ET-6 was 767.95, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 767, so it was identified as compound ET-6. .

Synthesis Example 7 (synthesis of compound ET-7)

ET- 7 was synthesized. The molecular weight of compound ET-7 was 727.87, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 727, so it was identified as compound ET-7. .

Synthesis Example 8 (synthesis of compound ET-8)

2,4-bis(4-biphenyl-yl)-6-chloro-1,3,5-triazine (5.0 g) and dibenzofuran-4-boronic acid (3.8 g) were added to dimethoxyethane (200 mL). , argon gas was bubbled through the solution for 5 minutes. Tetrakis(triphenylphosphine)palladium (0.55 g) and an aqueous sodium carbonate solution (2M, 18 mL) were added thereto, and the mixture was stirred under reflux with heating for 5 hours under an argon atmosphere. After cooling to room temperature, the precipitated solid was collected by filtration and washed with methanol and water. 200 mL of chlorobenzene was added to this solid and dissolved by heating, and the insoluble matter was removed by filtration through celite. Compound ET-8 was obtained by recrystallizing the solid precipitated by concentration under reduced pressure with toluene (5.3 g, yield 80%). The molecular weight of compound ET-8 was 551.65, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 551. Therefore, it was identified as compound ET-8. .

Synthesis Example 9 (synthesis of compound ET-9)
(1) Synthesis of intermediate H

Cyanuric chloride (9.3 g) and 2-biphenylboronic acid (9.9 g) were dissolved in toluene (250 mL), and argon gas was passed through the solution for 5 minutes. To this was added dichlorobis(triphenylphosphine)palladium (176 mg) and potassium carbonate (28 g) and heated to 60° C. for 4 hours with stirring under an argon atmosphere. The reaction solution was subjected to column chromatography to obtain Intermediate H (3.4 g, 23% yield).

(2) Synthesis of Intermediate I

Intermediate H (4.4 g) and 6-phenyl-2-naphthalenylboronic acid (synthesized according to Japanese Patent Publication 2010-241688A) (4.0 g) were added to toluene (73 mL), and argon gas was added to the solution. Got through for 5 minutes. To this was added dichlorobis(triphenylphosphine)palladium (10 mg) and aqueous sodium carbonate (2M, 22 mL) and heated to 65° C. overnight with stirring under an argon atmosphere. The reaction solution was subjected to column chromatography to obtain Intermediate I (2.9 g, yield 42%).

(3) Synthesis of compound ET-9

Intermediate I (2.9 g) and dibenzothiophene-4-boronic acid (2.1 g) were dissolved in dimethoxyethane (62 mL), tetrakis(triphenylphosphine)palladium (290 mg) was added, and the inside of the vessel was replaced with argon. . After that, a 2M sodium carbonate aqueous solution (9.3 mL) was added, and the mixture was heated under reflux for 3 hours under an argon atmosphere. After allowing the reaction solution to cool, the solid was collected by filtration. To this solid, 500 mL of toluene was added and heated to dissolve, and the insoluble matter was filtered off with silica gel. The solid precipitated by concentration under reduced pressure was recrystallized with toluene to obtain compound ET-9 (2.9 g, yield 76%). The molecular weight of compound ET-9 was 617.77, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 617, so it was identified as compound ET-9. .

Synthesis Example 10 (synthesis of compound ET-10)
(1) Synthesis of intermediate J

Intermediate H (5.2 g) and 4-1-(naphthalenyl)phenyl-boronic acid (synthesized according to Japanese Patent Publication 2013-546171A) (4.7 g) were added to toluene (86 mL), and argon gas was added to the solution. Got through for 5 minutes. To this was added dichlorobis(triphenylphosphine)palladium (12 mg) and aqueous sodium carbonate (2M, 21 mL) and heated to 60° C. overnight with stirring under an argon atmosphere. The reaction solution was subjected to column chromatography to obtain Intermediate J (7.1 g, yield 81%).

(2) Synthesis of compound ET-10

Intermediate J (7.0 g) and dibenzothiophene-4-boronic acid (5.1 g) were dissolved in dimethoxyethane (150 mL), tetrakis(triphenylphosphine)palladium (690 mg) was added, and the inside of the vessel was replaced with argon. . After that, a 2M sodium carbonate aqueous solution (19 mL) was added, and the mixture was heated under reflux for 3 hours under an argon atmosphere. After allowing the reaction solution to cool, the solid was collected by filtration. 580 mL of toluene was added to this solid and dissolved by heating, and the insoluble matter was filtered off with silica gel. Compound ET-10 was obtained by recrystallizing the solid precipitated by concentration under reduced pressure with toluene (9.2 g, yield 68%). The molecular weight of compound ET-10 was 617.77, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 617, so it was identified as compound ET-10. .

Synthesis Example 11 (synthesis of compound ET-11)
(1) Synthesis of intermediate K

Cyanuric chloride (9.3 g) and 3-biphenylboronic acid (9.9 g) were dissolved in toluene (250 mL), and argon gas was passed through the solution for 5 minutes. To this was added dichlorobis(triphenylphosphine)palladium (180 mg) and potassium carbonate (28 g) and heated to 60° C. for 4 hours with stirring under an argon atmosphere. The reaction solution was filtered and the filtrate was concentrated. The residue was subjected to column chromatography to give Intermediate K (5.9 g, 40% yield).

(2) Synthesis of intermediate L

Intermediate K (4.5 g) and naphthalene-1-boronic acid (2.8 g) were added to toluene (80 mL) and argon gas was bubbled through the solution for 5 minutes. To this was added dichlorobis(triphenylphosphine)palladium (10 mg) and aqueous sodium carbonate (2M, 25 mL) and heated to 60° C. overnight with stirring under an argon atmosphere. The reaction solution was subjected to column chromatography to obtain Intermediate L (3.5 g, yield 60%).

(3) Synthesis of compound ET-11

Intermediate L (3.5 g) and dibenzothiophene-4-boronic acid (3.0 g) were dissolved in dimethoxyethane (80 mL), tetrakis(triphenylphosphine)palladium (310 mg) was added, and the inside of the vessel was replaced with argon. . After that, a 2M sodium carbonate aqueous solution (11 mL) was added, and the mixture was heated under reflux for 3 hours under an argon atmosphere. After allowing the reaction solution to cool, the solid was collected by filtration. Toluene (700 mL) was added to this solid and dissolved by heating, and the insoluble matter was filtered off with silica gel. The solid precipitated by concentration under reduced pressure was recrystallized with toluene to obtain compound ET-11 (3.4 g, yield 71%). The molecular weight of the compound ET-11 was 541.67, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 541, so it was identified as the compound ET-11. .

Synthesis Example 12 (synthesis of compound ET-12)
(1) Synthesis of intermediate M

Cyanuric chloride (9.5 g) and 4-phenylnaphthalene-1-boronic acid (12 g) were dissolved in toluene (200 mL), and argon gas was passed through the solution for 5 minutes. To this was added dichlorobis(triphenylphosphine)palladium (190 mg) and potassium carbonate (31 g) and heated to 60° C. for 4 hours with stirring under an argon atmosphere. The reaction solution was filtered and the filtrate was concentrated. The residue was subjected to column chromatography to give Intermediate M (10 g, 55% yield).

(2) Synthesis of intermediate N

Intermediate M (8.2 g) and 3-(2-naphthyl)phenylboronic acid (6.4 g) were added to toluene (110 mL) and argon gas was bubbled through the solution for 5 minutes. To this was added dichlorobis(triphenylphosphine)palladium (21 mg) and aqueous sodium carbonate solution (2M, 20 mL) and heated to 60° C. overnight with stirring under an argon atmosphere. The reaction solution was subjected to column chromatography to obtain intermediate N (8.9 g, yield 73%).

(3) Synthesis of compound ET-12

Intermediate N (7.5 g) and dibenzothiophene-4-boronic acid (4.9 g) were dissolved in dimethoxyethane (130 mL), tetrakis(triphenylphosphine)palladium (420 mg) was added, and the inside of the vessel was replaced with argon. . After that, a 2M sodium carbonate aqueous solution (20 mL) was added, and the mixture was heated under reflux for 5 hours under an argon atmosphere. After allowing the reaction solution to cool, the solid was collected by filtration. Toluene (300 mL) was added to this solid and dissolved by heating, and the insoluble matter was removed by filtration through silica gel. Compound ET-12 was obtained by recrystallizing the solid precipitated by concentration under reduced pressure with toluene (4.1 g, yield 43%). The molecular weight of compound ET-12 was 667.83, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 667, so it was identified as compound ET-12. .

Synthesis Example 13 (synthesis of compound ET-13)
(1) Synthesis of intermediate O

2-(4-biphenylyl)-4,6-dichloro-1,3,5-triazine (5.6 g) and 3-(1-naphthyl)phenylboronic acid (4.5 g), dichlorobis(triphenylphosphine) palladium (24 mg) was dissolved in toluene (90 mL), and the inside of the container was replaced with argon. After that, 2M sodium carbonate aqueous solution (15 mL) was added, and the mixture was heated to 60° C. under an argon atmosphere and stirred overnight. Water was added to the reaction solution, and the precipitated solid was collected by filtration. The solid was dissolved in toluene, filtered and the filtrate was concentrated. The obtained solid was recrystallized with toluene to obtain intermediate O (6.0 g, yield 69%).

(2) Synthesis of compound ET-13

Intermediate O (5.3 g) and dibenzothiophene-4-boronic acid (3.9 g) were dissolved in dimethoxyethane (200 mL), tetrakis(triphenylphosphine)palladium (450 mg) was added, and the inside of the vessel was replaced with argon. . After that, a 2M sodium carbonate aqueous solution (17 mL) was added, and the mixture was heated under reflux for 6 hours under an argon atmosphere. After allowing the reaction solution to cool, the solid was collected by filtration. Toluene (620 mL) was added to this solid and dissolved by heating, and the insoluble matter was filtered off with silica gel. Compound ET-13 was obtained by recrystallizing the solid precipitated by concentration under reduced pressure with toluene (5.7 g, yield 82%). The molecular weight of compound ET-13 was 617.77, and the result of mass spectrum analysis of the obtained compound was m/z (mass-to-charge ratio) = 617, so it was identified as compound ET-13. .

Synthesis Example 14 (synthesis of compound ET-14)
(1) Synthesis of intermediate P

Intermediate H (6.3 g), 3-(1-naphthyl)phenylboronic acid (4.9 g), and dichlorobis(triphenylphosphine) palladium (15 mg) were dissolved in toluene (84 mL), and the inside of the vessel was replaced with argon. . After that, 2M sodium carbonate aqueous solution (14 mL) was added, and the mixture was heated to 60° C. under an argon atmosphere and stirred for 4 hours. Water was added to the reaction solution, and the precipitated solid was collected by filtration. The solid was dissolved in toluene, filtered and the filtrate was concentrated. The obtained solid was recrystallized with toluene to obtain intermediate P (6.3 g, yield 65%).

(2) Synthesis of compound ET-14

Intermediate P (5.6 g) and dibenzothiophene-4-boronic acid (4.1 g) were dissolved in dimethoxyethane (130 mL), tetrakis(triphenylphosphine)palladium (554 mg) was added, and the inside of the vessel was replaced with argon. . After that, a 2M sodium carbonate aqueous solution (15 mL) was added, and the mixture was heated under reflux for 4 hours under an argon atmosphere. After allowing the reaction solution to cool, the solid was collected by filtration. Toluene (350 mL) was added to this solid and dissolved by heating, and the insoluble matter was filtered off with silica gel. Compound ET-14 was obtained (6.5 g, yield 88%) by recrystallizing the solid precipitated by concentration under reduced pressure with toluene. The compound ET-14 had a molecular weight of 617.77, and the mass spectrum analysis result of the obtained compound was m/z (mass-to-charge ratio) = 617. Therefore, the compound was identified as ET-14. .

Example 1
(Production of organic EL element)
A 25 mm×75 mm×1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of ITO was set to 130 nm.
After washing, the glass substrate with the transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus. First, a compound HI was vapor-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode. A film was formed. This HI film functions as a hole injection layer.

Following the formation of this HI film, compound HT-1 was vapor-deposited to form an HT-1 film having a thickness of 80 nm on the HI film. This HT-1 film functions as a hole transport layer (first hole transport layer).
After forming the HT-1 film, the compound HT-2 was vapor-deposited to form an HT-2 film having a thickness of 10 nm on the HT-1 film. This HT-2 film functions as an electron blocking layer (second hole transport layer).
Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the HT-2 film so that the proportion of compound BD-1 was 4% by mass, and BH-1 having a thickness of 25 nm: A BD-1 film was formed. This BH-1:BD-1 film functions as a light-emitting layer.

Compound ET-1 and Liq were co-deposited on the light-emitting layer so that the ratio of Liq was 50% by mass to form an ET-1:Liq film with a thickness of 25 nm. This ET-1:Liq film functions as a first electron transport layer (hole blocking layer).
Liq was vapor-deposited on this first electron transport layer to form a Liq film with a thickness of 1 nm. This Liq film functions as a second electron transport layer.
Metal Al was vapor-deposited on the second electron transport layer to form a metal cathode having a thickness of 80 nm, thereby fabricating an organic EL device.

The layer structure of the obtained organic EL element is as follows.
ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / BH-1: BD-1 (25; 4 wt%) / ET-1: Liq (25; 50 wt% )/Liq(1)/Al(80)
The numbers in parentheses represent the film thickness (unit: nm).

(Evaluation of organic EL element)
The initial characteristics of the resulting organic EL device were measured at room temperature with a DC (direct current) constant current of 10 mA/cm ² driven. Table 1 shows the measurement results of the drive voltage.
A voltage was applied to the organic EL element so that the current density was 10 mA/cm ² , and the EL emission spectrum was measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta, Inc.). External quantum efficiency EQE (%) was calculated from the obtained spectral radiance spectrum. Table 1 shows the results.

Examples 2 to 8 and Comparative Example 1
An organic EL device was produced and evaluated in the same manner as in Example 1, except that the compounds shown in Table 1 were used as the material for the first electron transport layer. Table 1 shows the results.

The compounds used in Examples 1 to 8 and Comparative Example 1 are as follows.

From the results in Table 1, it can be seen that the organic EL devices of Examples 1 to 8 using a specific compound in the first electron-transporting layer exhibit higher external quantum efficiencies than the organic EL device of Comparative Example 1. .

Example 9
(Production of organic EL element)
A 25 mm×75 mm×1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of ITO was set to 130 nm.
After washing, the glass substrate with the transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and compound HT-3 and HI-2 were added to the surface on which the transparent electrode was formed so as to cover the transparent electrode. A HT-3:HI-2 film with a thickness of 5 nm was formed by co-evaporation so that the proportion (mass ratio) of HI-2 was 3%. This HT-3:HI-2 film functions as a hole injection layer.

After forming the HT-3:HI-2 film, the compound HT-3 was vapor-deposited to form an HT-3 film having a thickness of 90 nm on the HT-3:HI-2 film. This HT-3 film functions as the first hole transport layer.
After forming the HT-3 film, the compound EB was vapor-deposited to form an EB film having a thickness of 5 nm on the HT-3 film. This EB film functions as a second hole transport layer.
Compound BH-2 (host material) and compound BD-2 (dopant material) were co-evaporated on the EB film so that the ratio (mass ratio) of compound BD-2 was 4%, and BH-2 having a thickness of 20 nm was formed. : A BD-2 film was formed. This BH-2:BD-2 film functions as a light-emitting layer.

A compound HB was vapor-deposited on this light-emitting layer to form an HB film having a thickness of 5 nm. This HB film functions as a first electron transport layer. Following the formation of the HB film, the compounds ET-1 and Liq were co-evaporated so that the ratio (mass ratio) of Liq was 50% to form an ET-1:Liq film with a thickness of 20 nm. This ET-1:Liq film functions as a second electron transport layer. Liq was deposited on this ET-1:Liq film to form a Liq film with a thickness of 1 nm. Metal Al was vapor-deposited on this Liq film to form a metal cathode with a film thickness of 80 nm, thereby fabricating an organic EL device.

The layer structure of the obtained organic EL element is as follows.
ITO (130) / HT-3: HI-2 (5; 3% by mass) / HT-3 (90) / EB (5) / BH-2: BD-2 (20; 4% by mass) / HB (5 ) / ET-1: Liq (20; 50 mass%) / Liq (1) / Al (80)
The numbers in parentheses represent the film thickness (unit: nm).

(Evaluation of organic EL element)
A voltage was applied to the obtained organic EL element so that the current density was 10 mA/cm ² , and the EL emission spectrum was measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.). External quantum efficiency EQE (%) was calculated from the obtained spectral radiance spectrum. Table 2 shows the results.

Examples 10-12
An organic EL device was produced and evaluated in the same manner as in Example 9 except that the compounds shown in Table 2 were used as the host material of the light-emitting layer. Table 2 shows the results.

The compounds used in Examples 9-12 are as follows.

From the results in Tables 1 and 2, the compound in which one dibenzothiophene ring was bonded to the 4-position of the azine ring was added to the electron transport zone (the first electron transport layer in Examples 1 to 8, and the second electron transport layer in Examples 9 to 12). 2 electron transport layer), the luminous efficiency is improved.

Further, from the results in Table 2, host materials (compounds BH-2 to BH-5) having a dibenzofuran ring as a side chain, which are different from the host materials (compound BH-1) used in the devices of Examples 1 to 8, were used. It was found that high external quantum efficiency was obtained also in the case of using (Examples 9 to 12).

Although several embodiments and/or examples of the present invention have been described above in detail, those of ordinary skill in the art may modify these exemplary embodiments and/or examples without departing substantially from the novel teachings and advantages of the present invention. It is easy to make many modifications to the examples. Accordingly, many of these variations are included within the scope of the present invention.
The documents mentioned in this specification and the contents of the applications from which this application has priority under the Paris Convention are incorporated in their entirety.

Claims (27)

A compound represented by the following formula (6) or (8) .

(In formula ( 6 ),
X ₁ is O or S;
Y ₁ , Y ₂ and Y ₃ are each independently CH or N;
provided that two or more of Y ₁ , Y ₂ and Y ₃ are N;
Ar ₁ is
single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
It is a substituted or unsubstituted phenanthrylene group or a substituted or unsubstituted anthrylene group.
Ar _3A is a phenylene group, naphthylene group, phenanthrylene group, or anthrylene group comprising a benzene ring substituted with Ar ₄ at least at the ortho position , and has one or more substituents other than Ar ₄ ; may be
Ar ₂ and Ar ₄ are each independently
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted anthryl group,
is.
Ar ₁ and Ar ₂ are bonded to each other to form a ring consisting only of a substituted or unsubstituted saturated or unsaturated 6-membered ring, or do not form a ring.
However, the case where —Ar ₁ —Ar ₂ is the following group is excluded.

(In Formula (8), X ₁ , Y ₁ , Ar ₂ and Ar ₄ are as defined in Formula (6) above.
Ar _1D and Ar _3D are each independently a divalent group selected from the following group.

(Wherein, _Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
q is an integer from 0 to 2;
When there are 2 or more Ras , the two or more _Ras may be the same or different _.
When there are 2 or more R _a , two or more adjacent R _a pairs do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. )) Ar ₂ and Ar ₄ are each independently
an unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
2. The compound according to claim 1, which is a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted anthryl group. When Ar ₁ and Ar _3A are unsubstituted phenylene groups, or Ar _1D and Ar _3D are unsubstituted phenylene groups , Ar ₂ and Ar ₄ are each independently
an unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
3. The compound according to claim 1 or 2, which is a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted anthryl group. The compound according to any one of claims 1 to 3 , wherein Ar ₁ and Ar ₂ are not joined together to form a ring. When Ar ₁ , Ar ₂ , Ar ₄ , Ar _3A , Ar _1D , and Ar _3D are substituted, the substituents are
an unsubstituted phenyl group,
an unsubstituted naphthyl group,
an unsubstituted phenanthryl group,
an unsubstituted anthryl group,
an unsubstituted biphenyl group,
The compound according to any one of claims 1 to 4, which is an unsubstituted alkyl group having 1 to 50 carbon atoms or an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms. 6. The compound according to any one of claims 1 to 5, wherein -Ar ₁ -Ar ₂ is selected from the group consisting of groups represented by the following formulas (a1) to (a11).

(In the formulas (a1) to (a11),
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each m is independently an integer of 0 to 5.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
Each q is independently an integer of 0 to 2.
r is an integer of 0 or 1;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. ) 7. The compound according to any one of claims 1 to 6, wherein -Ar ₁ -Ar ₂ is selected from the group consisting of groups represented by the following formulas (aa1) to (aa8).

(In the formulas (aa1) to (aa8),
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each m is independently an integer of 0 to 5.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
q is an integer from 0 to 2;
r is an integer of 0 or 1;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. ) 8. The compound according to any one of claims 1 to 7, wherein -Ar ₁ -Ar ₂ is selected from the group consisting of groups represented by the following formulas (ab1) to (ab7).

(In the formulas (ab1) to (ab7),
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each m is independently an integer of 0 to 5.
Each n is independently an integer of 0-4.
p is an integer from 0 to 3;
q is an integer from 0 to 2;
r is an integer of 0 or 1;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. ) 6. The compound according to any one of claims 1 to 5, wherein -Ar ₁ -Ar ₂ is selected from the group consisting of groups represented by the following formulas (ac1) to (ac93).

(In formulas (ac1) to (ac93),
_Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
A substituted or unsubstituted anthryl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each m is independently an integer of 0 to 5.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
Each q is independently an integer of 0 to 2.
Each r is independently an integer of 0 or 1.
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. ) 10. The compound according to any one of claims 6 to 9, wherein one or more pairs of two or more adjacent R _a do not combine with each other to form a ring. Ar ₂ and Ar ₄ are each independently
an unsubstituted phenyl group,
an unsubstituted naphthyl group,
The compound according to any one of claims 1 to 10, which is an unsubstituted anthryl group or an unsubstituted phenanthryl group. A compound according to any of claims 1-11, wherein X ₁ is S. A compound according to any of claims 1-12, wherein Y ₁ -Y ₃ are N. The compound according to claim 1 , wherein the compound represented by the formula ( 6 ) is a compound represented by the following formula (6-1).

[In the formula (6-1), X ₁ , Y ₁ to Y ₃ , Ar ₂ , Ar ₄ and Ar _3A are as defined in the formula ( 6 ) .
A r _1a is a divalent group selected from the following group.

(Wherein, _Ra is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted anthryl group,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
Each n is independently an integer of 0-4.
Each p is independently an integer of 0-3.
q is an integer from 0 to 2;
When there are 2 or more _Ras , the two or more _Ras may be the same or different.
When there are two or more R _a , two or more pairs of adjacent R _a are bonded together to form a substituted or unsubstituted saturated or unsaturated ring or do not form a ring. )] An electron-transporting material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 14 . An organic electroluminescence device comprising an anode, an organic layer, and a cathode in this order,
wherein the organic layer comprises a compound according to any one of claims 1-14 ,
Organic electroluminescence device. An organic electroluminescent device comprising an anode, a light-emitting layer, an electron-transporting zone, and a cathode in this order,
An organic electroluminescent device, wherein said electron-transporting zone comprises a compound according to any one of claims 1-14 . wherein the electron-transporting zone comprises the first electron-transporting layer and the second electron-transporting layer in the order of the light-emitting layer, the first electron-transporting layer, the second electron-transporting layer and the cathode;
18. The organic electroluminescence device according to claim 17 , wherein at least one of the first electron transport layer and the second electron transport layer comprises the compound according to any one of claims 1-14 . 19. The organic electroluminescence device according to claim 17 , wherein the light-emitting layer contains a compound represented by the following formula (11).

(In formula (11),
R ₁₁ to R ₁₈ are each independently
hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are each independently
hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more R ₉₀₁ to R ₉₀₇ are present, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different.
Two or more adjacent ones of R ₁₁ to R ₁₄ and two or more adjacent ones of R ₁₅ to R ₁₈ do not combine to form a ring.
L ₁₁ and L ₁₂ are each independently
single bond,
It is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
Ar ₁₁ and Ar ₁₂ are each independently
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. ) 20. The organic electroluminescence device according to claim 19 , wherein the compound represented by formula (11) is a compound represented by formula (12) below.

[In Formula (12), R ₁₁ to R ₁₈ , L ₁₁ and L ₁₂ are as defined in Formula (11) above.
At least one of Ar _11a and Ar _12a is a monovalent group represented by the following formula (20).

(In formula (20),
one of R ₂₁ to R ₂₈ is a bond that binds to L ₁₁ or L ₁₂ ;
R ₂₁ to R ₂₈ that are not bonds that bind to L ₁₁ or L ₁₂ are
each independently a hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in formula (11) above.
Adjacent two or more of R ₂₁ to R ₂₈ which are not bonds to L ₁₁ or L ₁₂ do not bond to each other to form a ring. )
Ar _11a or Ar _12a , which is not a monovalent group represented by the formula (20),
A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms other than the monovalent group represented by the formula (20) It is a cyclic group. ] 21. The organic electroluminescence device according to claim 20 , wherein the compound represented by formula (12) is a compound represented by formula (12-1) below.

(In Formula (12-1), R ₁₁ to R ₁₈ , L ₁₁ and L ₁₂ are as defined in Formula (11) above.
Ar _12a is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted 5 to 50 ring-forming atoms other than the monovalent group represented by the formula (20) It is a monovalent heterocyclic group.
R ₂₁ and R ₂₃ to R ₂₈ are each independently a hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
—Si(R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O—(R ₉₀₄ ),
-S-(R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in formula (11) above. ) 20. The organic electroluminescence device according to claim 19 , wherein the compound represented by formula (11) is a compound represented by formula (13) below.

(In Formula (13), R ₁₁ to R ₁₈ , L ₁₁ and L ₁₂ are as defined in Formula (11) above.
Ar _11b and Ar _12b are each independently a substituted or unsubstituted aryl group consisting of a benzene ring having 6 to 50 ring-forming carbon atoms. ) 23. The organic electroluminescence device according to claim 22 , wherein the compound represented by formula (13) is a compound represented by formula (13-1) below.

(In formula (13-1), R ₁₁ to R ₁₈ and L ₁₂ are as defined in formula (11) above.
Ar _11b and Ar _12b are each independently a substituted or unsubstituted aryl group consisting of a benzene ring having 6 to 50 ring-forming carbon atoms. ) Ar _11b and Ar _12b are each independently
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted biphenylyl group,
24. The organic electroluminescence device according to claim 22 , which is a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted anthryl group, or a substituted or unsubstituted phenanthryl group. Either one or both of the first electron-transporting layer and the second electron-transporting layer may further contain an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, or an alkaline earth metal. Oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal-containing organic complexes, alkaline earth metal-containing organic complexes, and rare earth metal-containing organic complexes 25. The organic electroluminescence device according to any one of claims 18 to 24 , containing one or more selected from the group consisting of 26. The organic electroluminescence device according to claim 17 , comprising a hole transport layer between said anode and said light emitting layer. An electronic device comprising the organic electroluminescence device according to any one of claims 17 to 26 .

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